CN108084110A - 3- amino benzo [d] isothiazole, derivative and its synthetic method - Google Patents
3- amino benzo [d] isothiazole, derivative and its synthetic method Download PDFInfo
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- CN108084110A CN108084110A CN201711399099.7A CN201711399099A CN108084110A CN 108084110 A CN108084110 A CN 108084110A CN 201711399099 A CN201711399099 A CN 201711399099A CN 108084110 A CN108084110 A CN 108084110A
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- benzenecarboximidamide
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
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Abstract
The invention mainly relates to a kind of 3 amino benzo [d] isothiazole and its derivative and its synthetic methods, catalyst need not be used during synthesis, only under the action of alkali and in air atmosphere, benzenecarboximidamide class compound and elemental sulfur are converted into the technical solution of 3 amino benzo [d] isothiazole and its derivative；The synthetic method that it overcomes existing capabilityization 3 amino benzo [d] isothiazole compounds is complicated there are synthesis step, it needs to take multi-step synthetic process that could complete, it also needs to metallic catalyst either peroxide and yield is relatively low or severe reaction conditions problem.The present invention has the characteristics that reaction system is simple, reaction condition is mild, consersion unit is less, experimental implementation is easy, materials derive from a wealth of sources, yield is high, user and application is easy to extension, product utilization is worth higher, market business prospect and is expected.
Description
Technical field
The present invention relates to a kind of organic compound and its synthetic method, particularly a kind of 3- amino benzo [d] isothiazole, spread out
Biology and its synthetic method.
Background technology
3- amino benzo [d] Isothizole derivatives are natural products, common in drug and many other bioactive products
Peculiar primitive.However, it is considerably less to be effectively used for benzisothiazole synthetic method.With 3- amino benzo [d] isothiazole
Chloride is raw material, and using 3- amino benzo [d] different thiazoles compound as primary raw material, one has been synthesized by S-N bonding reactions
Serial benzisothia trazodone derivative (thio-methyl salicylate) is between SH and NH groups) use hypervalent iodine reagent PIFA [(benzene
Base iodine (III) is double (trifluoroacetate)] it is used as oxidant.Recently, Yadav and his colleague develop it is a kind of by 2- amino-N '-
Aryl-benzoyl hydrazine is as raw material, and using Lawesson reagents as sulphur source, this method, which is primarily adapted for use in, prepares 3- substitution benzos
[c] isothiazole.It is highly desirable to prepare various substituted 1,2- benzisothiazole prepared products under simple and mild reaction condition.
So far, it is report that raw material directly synthesizes 3- amino benzo [d] isothiazole not with elemental sulfur.
The content of the invention
It is therefore an object of the present invention to provide a kind of 3- amino benzo [d] isothiazole and its derivative.
It is yet another object of the invention to provide the synthetic method of a kind of 3- amino benzo [d] isothiazole and its derivative, tools
There is the advantages of simple for process, yield is high.
So as to which a kind of 3- amino benzo [d] isothiazole of the invention and its derivative, its general formula are Formulas I：
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl；
The present invention also provides a kind of method of 3- amino benzo [d] isothiazole and its derivative, by benzenecarboximidamide class compound
With elemental sulfur is heated under the reaction condition of inorganic base and organic solvent stirs to get.
Preferably, method of the invention, the cloth inorganic base are selected from KHCO3、K2CO3、Na2CO3、K3PO4、K2HPO4、KOH、
NaOH、Cs2CO3, potassium tert-butoxide, sodium tert-butoxide, sodium ethoxide, the one or more of sodium methoxide.
Preferably, method of the invention, the organic solvent be selected from adjoin pyridine, acetonitrile, THF, DMAC, DMF, DMSO, Isosorbide-5-Nitrae-
One or more in dioxane, toluene.
Preferably, method of the invention, the benzenecarboximidamide class compound, elemental sulfur, the molar ratio of alkali are 1: 5: 2-3, instead
It is 110 DEG C -140 DEG C to answer temperature.
Preferably, method of the invention, the benzamidine compound are selected from C7-C19 fragrance amidines, and general formula is Formula II：
Wherein
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl；
X is selected from fluorine atom, chlorine atom, bromine atoms.
Benzenecarboximidamide class compound in Formula II is selected from benzenecarboximidamide, 2- fluorobenzene carbonamidines, 2- chlordimeforms, 2- bromobenzene carbonamidines, 2-
Fluoro- N- phenyl benzenecarboximidamide, the chloro- N- phenyl benzenecarboximidamides of 2-, the bromo- N- phenyl benzenecarboximidamides of 2-, 2- chloro- N- (p-methylphenyl) benzenecarboximidamide,
The chloro- N- of 2- (4- ethylphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- (tertiary butyl) phenyl) benzenecarboximidamide, the chloro- N- of 2- (4- methoxyphenyls)
Benzenecarboximidamide, the chloro- N- of 2- (4- ethoxyl phenenyls) benzenecarboximidamide, the chloro- N- of 2- (4- Trifluoromethoxyphen-ls) benzenecarboximidamide, the chloro- N- (4- of 2-
Fluorophenyl) benzenecarboximidamide, the chloro- N- of 2- (4- chlorphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- bromophenyls) benzenecarboximidamide, the chloro- N- of 2- ([1,1 '-
Biphenyl] -4- bases) benzenecarboximidamide, the chloro- N- of 2- (naphthalene -2- bases) benzenecarboximidamide, the chloro- N- of 2- (m- tolyl) benzenecarboximidamide, the chloro- N- of 2- are (m-
Ethylbenzene) benzenecarboximidamide, the chloro- N- of 2- (3- chlorphenyls) benzenecarboximidamide, the chloro- N- of 2- (o- tolyl) benzenecarboximidamide, the chloro- N- of 2- (2,4- bis-
Aminomethyl phenyl) benzenecarboximidamide, the chloro- N- of 2- (3,4- Dimethoxyphenyl) benzenecarboximidamide, the chloro- N- of 2- (3,4,5- trimethoxyphenyl) benzene
Carbonamidine, the chloro- 4- Methyl-N-phenyls benzenecarboximidamides of 2-, the chloro- 3- Methyl-N-phenyls benzenecarboximidamides of 2-, the fluoro- N- phenyl benzene first of the chloro- 4- of 2-
Amidine, the chloro- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the bromo- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the bromo- N- phenyl benzenecarboximidamides of the chloro- 5- of 2-, 2- are chloro-
5- trifluoromethyl-N- phenyl benzenecarboximidamides, the chloro- 4- trifluoromethyls-N- phenyl benzenecarboximidamides of 2-, 2- chloro-n-methyl-N- phenyl benzene first
Amidine.
Technical solution of the present invention has the following advantages that：
The compound of the present invention 3- amino benzo [d] isothiazole and its derivative synthesizing process need not use catalyst,
Only under the action of alkali, make solvent with organic solvent, it is different that benzenecarboximidamide class compound and elemental sulfur are converted into 3- amino benzo [d]
Thiazole and its derivative；It overcomes the synthetic method of existing 3- amino benzo [d] different thiazoles compound, and there are synthesis steps
Complexity is, it is necessary to take multi-step synthetic process that could complete, it is also necessary to metallic catalyst, stoichiometric peroxide it is tired
It is difficult；It is excellent with molecular structure stabilized, chemical property, and molecule stripping and slicing and compound segment include abundant bioactivity and medicine
Manage active content；It is also with reaction system is simple, reaction condition is mild, consersion unit is less, experimental implementation is easy, materials are next
It is special that source is extensive, yield is high, user and application are easy to extension, product utilization value is higher, market business prospect is expected etc.
Point.
Description of the drawings
In order to prove the product of the present invention, the nucleus magnetic hydrogen spectrum figure of section Example of the present invention and nuclear-magnetism carbon spectrogram.
The nucleus magnetic hydrogen spectrum figure of 1 product of Fig. 1-1 embodiments.
The nuclear-magnetism carbon spectrogram of 1 product of Fig. 1-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 2 product of Fig. 2-1 embodiments.
The nuclear-magnetism carbon spectrogram of 2 product of Fig. 2-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 3 product of Fig. 3-1 embodiments.
The nuclear-magnetism carbon spectrogram of 3 product of Fig. 3-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 4 product of Fig. 4-1 embodiments.
The nuclear-magnetism carbon spectrogram of 4 product of Fig. 4-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 5 product of Fig. 5-1 embodiments.
The nuclear-magnetism carbon spectrogram of 5 product of Fig. 5-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 6 product of Fig. 6-1 embodiments.
The nuclear-magnetism carbon spectrogram of 6 product of Fig. 6-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 7 product of Fig. 7-1 embodiments.
The nuclear-magnetism carbon spectrogram of 7 product of Fig. 7-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 8 product of Fig. 8-1 embodiments.
The nuclear-magnetism carbon spectrogram of 8 product of Fig. 8-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 9 product of Fig. 9-1 embodiments.
The nuclear-magnetism carbon spectrogram of 9 product of Fig. 9-2 embodiments.
The nucleus magnetic hydrogen spectrum figure of 10 product of Figure 10-1 embodiments.
The nuclear-magnetism carbon spectrogram of 10 product of Figure 10-2 embodiments.
Figure 11 is the reaction principle figure of the present invention.
Specific embodiment
Technical scheme is clearly and completely described below in conjunction with attached drawing, it is clear that described implementation
Example is part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill
Personnel's all other embodiments obtained without making creative work, belong to the scope of protection of the invention.
As long as in addition, technical characteristic involved in invention described below different embodiments non-structure each other
It can be combined with each other into conflict.
With reference to the synthetic route of the compounds of this invention, 3- amino benzo [d] isothiazole and its derivative composition principle, it is wrapped
Catalyst need not be used for the first time by including, only under the action of alkali, with pyridine, acetonitrile, THF, DMAC, DMF, DMSO, Isosorbide-5-Nitrae-dioxy
The organic solvents such as six rings, toluene make solvent, by benzenecarboximidamide class compound and elemental sulfur be converted into 3- amino benzo [d] isothiazole and
The technical solution of its derivative；There is synthesis in the synthetic method that it overcomes existing 3- amino benzo [d] different thiazoles compound
Step complexity is, it is necessary to take multi-step synthetic process that could complete, it is also necessary to metallic catalyst, stoichiometric peroxide
It is difficult；It has that molecular structure stabilized, chemical property are excellent, molecule stripping and slicing and compound segment include abundant bioactivity and
Pharmacological activity content；It is also with reaction system is simple, reaction condition is mild, consersion unit is less, experimental implementation is easy, materials
It derives from a wealth of sources, yield is high, user and application are easy to extension, product utilization value is higher, market business prospect is expected
Feature.
3- amino benzo [d] isothiazole and its derivative, its general formula are Formulas I：
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl；
In order to realize the method for synthesis 3- amino benzo [d] isothiazole and its derivative, under the action of alkali, by benzenecarboximidamide
Class compound and elemental sulfur are mixed with organic solvent to be reacted, purifies to obtain product.
In order to improve the comprehensive performance of the present invention, structure, effect optimization are realized, further step is：
The alkali is selected from KHCO3、K2CO3、Na2CO3、K3PO4、K2HPO4、KOH、NaOH、Cs2CO3, potassium tert-butoxide, tertiary fourth
Sodium alkoxide, sodium ethoxide, the one or more of sodium methoxide；The organic agent for pyridine, acetonitrile, THF, DMAC, DMF, DMSO, Isosorbide-5-Nitrae-
Dioxane, toluene, the benzenecarboximidamide class compound, elemental sulfur, the molar ratio of alkali are 1: 5: 2, and reaction temperature is 135 DEG C.
The benzenecarboximidamide class compound is selected from C7-C19 fragrance amidines, and general formula is as follows：
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl；
X is selected from fluorine atom, chlorine atom, bromine atoms.
Benzenecarboximidamide class compound in Formula II preferably is selected from benzenecarboximidamide, 2- fluorobenzene carbonamidines, 2- chlordimeforms, 2- bromobenzene carbonamidines,
The fluoro- N- phenyl benzenecarboximidamides of 2-, the chloro- N- phenyl benzenecarboximidamides of 2-, the bromo- N- phenyl benzenecarboximidamides of 2-, 2- chloro- N- (p-methylphenyl) benzene first
Amidine, the chloro- N- of 2- (4- ethylphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- (tertiary butyl) phenyl) benzenecarboximidamide, 2- chloro- N- (4- methoxybenzenes
Base) benzenecarboximidamide, the chloro- N- of 2- (4- ethoxyl phenenyls) benzenecarboximidamide, the chloro- N- of 2- (4- Trifluoromethoxyphen-ls) benzenecarboximidamide, the chloro- N- of 2-
(4- fluorophenyls) benzenecarboximidamide, the chloro- N- of 2- (4- chlorphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- bromophenyls) benzenecarboximidamide, the chloro- N- of 2- ([1,
1 '-biphenyl] -4- bases) benzenecarboximidamide, the chloro- N- of 2- (naphthalene -2- bases) benzenecarboximidamide, the chloro- N- of 2- (m- tolyl) benzenecarboximidamide, the chloro- N- of 2-
(m- ethylbenzene) benzenecarboximidamide, the chloro- N- of 2- (3- chlorphenyls) benzenecarboximidamide, the chloro- N- of 2- (o- tolyl) benzenecarboximidamide, the chloro- N- of 2- (2,
4- 3,5-dimethylphenyls) benzenecarboximidamide, the chloro- N- of 2- (3,4- Dimethoxyphenyl) benzenecarboximidamide, 2- chloro- N- (3,4,5- trimethoxy-benzenes
Base) benzenecarboximidamide, the chloro- 4- Methyl-N-phenyls benzenecarboximidamides of 2-, the chloro- 3- Methyl-N-phenyls benzenecarboximidamides of 2-, the fluoro- N- phenyl of the chloro- 4- of 2-
Benzenecarboximidamide, the chloro- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the bromo- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the bromo- N- phenyl benzenecarboximidamides of the chloro- 5- of 2-,
The chloro- 5- trifluoromethyls-N- phenyl benzenecarboximidamides of 2-, the chloro- 4- trifluoromethyls-N- phenyl benzenecarboximidamides of 2-, 2- chloro-n-methyl-N- phenyl
Benzenecarboximidamide.
3- amino benzo [d] isothiazole is formed by Formula II and its derivative synthesizes the reaction system general formula of the present invention, such as：
Comprise the following steps：
(1) alkali, benzenecarboximidamide class compound, elemental sulfur and organic solvent are added in reaction vessel；
(2) after reactant is sufficiently mixed, heated；
(3) purified to obtain product after reacting；
Wherein, organic solvent is polar organic solvent, such as：Pyridine, acetonitrile, THF, DMAC, DMF, DMSO, Isosorbide-5-Nitrae-dioxy six
Ring, toluene；
It is preferred that DMSO, toluene, volume ratio 1: 2；
In order to reach better synthetic effect, the preferably molar ratio of benzamidine compound, elemental sulfur and alkali is 1: 3-5: 2-
3, preferred plan preferably 1: 5: 2；
Alkali used is KHCO3、K2CO3、Na2CO3、K3PO4、K2HPO4、KOH、NaOH、Cs2CO3, potassium tert-butoxide, the tert-butyl alcohol
Sodium, sodium ethoxide, the one or more of sodium methoxide；
Particularly preferred K3PO4；
The temperature T of reaction is 110 DEG C -140 DEG C；
Preferably 135 DEG C.
Can be drawn from the synthetic reaction plant process of the invention described above compound, 3- amino benzo [d] isothiazole and
Its derivative, it is need not to use catalyst for the first time, it is only necessary under conditions of alkali, benzenecarboximidamide class chemical combination and elemental sulfur be turned
Turn to 3- amino benzo [d] isothiazole.
For above-mentioned compound of formula I as a kind of important molecule stripping and slicing, its molecular structure stabilized, chemical property are excellent,
Body has certain physiological activity, can also further be synthesized by the conversion to functional group much different containing 3- amino benzo [d]
The compound segment of thiazole structure should have very strong physiological activity containing the compound of 3- amino benzo [d] isothiazole structure
And pharmacological activity；
In short, the compounds of this invention has reaction raw materials cheap and easy to get and need not be pre-processed；Reaction need not make
With catalyst and peroxide；It only needs that alkali is used to react the features such as directly synthesizing for one pot as accelerating agent；It is solved
The problems such as the existing cost brought using multi-step synthetic methods is higher；Its reaction condition is mild, and reaction required temperature is significantly less than
The reaction temperature of previous multistep synthesis；A series of 3- amino benzo [d] different thiazoles compounds of synthesis have quite high latent
In application value.
Embodiment 1-29
Embodiment 1-29 is synthesized using following steps：
(1) alkali, benzenecarboximidamide class compound, elemental sulfur and organic solvent are added in reaction vessel；
(2) after reactant is sufficiently mixed, heated；
(3) purified to obtain product after reacting；
Shown in benzenecarboximidamide class compound and reaction condition are shown in Table.
Table：Reactant, reaction condition and the yield of embodiment 1-29
It is to be noted that the reaction time is not only 36h, and it can be very long, here merely to comparing yield and setting
Using 36h as standard.
The nuclear-magnetism and mass spectrometric data of the product of section Example be：
The nuclear-magnetism and mass spectrometric data of 1 product of embodiment are as follows：
1H NMR (400MHz, DMSO-d6, ppm) and δ 9.60 (s, 1H), 8.49 (d, J=8.1Hz, 1H), 8.06 (d, J=
8.1Hz, 1H), 7.96 (d, J=7.7Hz, 2H), 7.60 (t, J=7.5Hz, 1H), 7.51 (t, J=7.5Hz, 1H), 7.34 (t,
J=8.0Hz, 2H), 6.97 (t, J=7.3Hz, 1H)；13C NMR (100MHz, DMSO-d6, ppm) and δ 155.3,149.9,
141.3,128.8,128.5,127.5,124.5,122.8,121.4,120.6,117.9；HRMS calcd.for：C13H11N2S
[M+H]+227.0638 found 227.0636.
The nuclear-magnetism and mass spectrometric data of 2 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.83 (d, J=8.1Hz, 1H), 7.77 (d, J=8.1Hz, 1H), 7.61
(d, J=8.3Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7.40 (t, J=7.5Hz, 1H), 7.17 (d, J=8.2Hz, 2H),
6.98 (s, 1H), 2.33 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.7,151.0,137.7,131.9,129.6,
128.1,127.0,124.1,120.8,120.4,118.5,20.8；HRMS calcd.for：C14H13N2S[M+H]+
241.0794 found 241.0790.
The nuclear-magnetism and mass spectrometric data of 3 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.1Hz, 1H), 7.77 (d, J=8.7Hz, 1H), 7.64
(d, J=8.5Hz, 2H), 7.52 (t, J=7.6Hz, 1H), 7.41 (t, J=7.6Hz, 1H), 7.20 (d, J=8.2Hz, 2H),
6.98 (s, 1H), 2.64 (q, J=7.6Hz, 2H), 1.24 (t, J=7.6Hz, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ
154.6,151.0,138.4,137.8,128.4,128.1,127.0,124.1,120.8,120.4,118.5,28.2,15.7；
HRMS calcd.for：C15H15N2S[M+H]+255.0951 found 255.0949.
The nuclear-magnetism and mass spectrometric data of 4 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.1Hz, 1H), 7.78 (d, J=8.1Hz, 1H), 7.65
(d, J=8.4Hz, 2H), 7.52 (t, J=7.6Hz, 1H), 7.43-7.35 (m, 3H), 6.98 (s, 1H), 1.33 (s, 9H)；13C
NMR (100MHz, CDCl3, ppm) and δ 154.6,151.0,145.3,137.6,128.1,127.0,125.9,124.1,120.8,
120.4,118.1,34.2,31.4；HRMS calcd.for：C17H19N2S[M+H]+283.1264 found 283.1264.
The nuclear-magnetism and mass spectrometric data of 5 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.80 (d, J=8.1Hz, 1H), 7.73 (d, J=8.1Hz, 1H), 7.64-
7.57 (m, 2H), 7.49 (t, J=7.3Hz, 1H), 7.36 (t, J=7.5Hz, 1H), 6.96-6.84 (m, 3H), 3.78 (s,
3H)；13C NMR (100MHz, CDCl3, ppm) and δ 155.3,155.1,151.0,133.6,128.0,126.9,124.0,120.8,
120.4,120.3,114.3,55.5；HRMS calcd.for：C14H13N2OS[M+H]+257.0743 found 257.0743.
The nuclear-magnetism and mass spectrometric data of 6 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.80 (d, J=8.1Hz, 1H), 7.72 (d, J=8.1Hz, 1H), 7.64-
7.55 (m, 2H), 7.49 (t, J=7.5Hz, 1H), 7.35 (t, J=7.5Hz, 1H), 6.98-6.83 (m, 3H), 4.00 (q, J=
7.0Hz, 2H), 1.39 (t, J=7.0Hz, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 155.1,154.6,151.0,
133.5,128.0,126.9,124.0,120.9,120.4,120.3,115.0,63.7,14.8；HRMS calcd.for：
C15H15N2OS[M+H]+271.0900 found 271.0894.
The nuclear-magnetism and mass spectrometric data of 7 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.1Hz, 1H), 7.82-7.72 (m, 3H), 7.53 (t, J
=7.6Hz, 1H), 7.41 (t, J=7.5Hz, 1H), 7.19 (d, J=8.8Hz, 2H), 7.07 (s, 1H)；13C NMR (100MHz,
CDCl3, ppm) and δ 154.0,151.0,143.7 (q, J=1.7,1.7Hz), 139.0,128.3,126.9,124.3,121.9,
120.6,120.6 (q, J=254.7Hz), 120.5,118.9；HRMS calcd.for：C14H10F3N2OS[M+H]+
311.0461 found 311.0458.
The nuclear-magnetism and mass spectrometric data of 8 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.85 (d, J=8.1Hz, 1H), 7.77 (d, J=8.1Hz, 1H), 7.73-
7.66 (m, 2H), 7.56-7.52 (m, 1H), 7.44-7.40 (m, 1H), 7.10-7.03 (m, 2H), 6.98 (s, 1H)；13C NMR
(100MHz, CDCl3, ppm) and δ 158.3 (d, J=239.6Hz), 154.5,151.1,136.3 (d, J=2.5Hz), 128.3,
126.8,124.3,120.7,120.5,119.9 (d, J=7.7Hz), 115.7 (d, J=22.3Hz)；HRMS calcd.for：
C13H10FN2S[M+H]+245.0543 found 245.0543.
The nuclear-magnetism and mass spectrometric data of 9 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.86 (d, J=8.1Hz, 1H), 7.78 (d, J=8.1Hz, 1H), 7.71
(d, J=8.8Hz, 2H), 7.55 (t, J=7.6Hz, 1H), 7.43 (t, J=7.5Hz, 1H), 7.31 (d, J=8.7Hz, 2H),
7.07 (s, 1H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.0,151.0,138.8,129.0,128.3,126.9,
126.9,124.3,120.7,120.5,119.2；HRMS calcd.for：C13H10ClN2S[M+H]+261.0248, found
261.0244.
The nuclear-magnetism and mass spectrometric data of 10 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.85 (d, J=8.1Hz, 1H), 7.77 (d, J=8.0Hz, 1H), 7.66
(d, J=7.8Hz, 2H), 7.54 (t, J=7.5Hz, 1H), 7.48-7.38 (m, 3H), 7.01 (s, 1H)；13C NMR (100MHz,
CDCl3, ppm) and δ 153.9,151.0,139.3,131.9,128.3,126.9,124.3,120.6,120.5,119.5,114.3；
HRMS calcd.for：C13H10BrN2S[M+H]+304.9743, found304.9746.
The nuclear-magnetism and mass spectrometric data of 11 product of embodiment are as follows：
1H NMR (400MHz, DMSO-d6, ppm) and δ 9.75 (s, 1H), 8.53 (d, J=8.1Hz, 1H), 8.08 (d, J=
8.8Hz, 3H), 7.70-7.67 (m, 4H), 7.63 (t, J=7.5Hz, 1H), 7.54 (t, J=7.5Hz, 1H), 7.45 (t, J=
7.6Hz, 2H), 7.32 (t, J=7.3Hz, 1H)；13C NMR (100MHz, DMSO-d6, ppm) and δ 155.29,149.99,140.9,
140.1,133.0,129.0,128.6,127.6,127.0,126.8,126.2,124.5,122.8,120.7,118.2；HRMS
calcd.for：C19H15N2S[M+H]+303.0951 found 303.0946.
The nuclear-magnetism and mass spectrometric data of 12 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 8.53 (d, J=1.7Hz, 1H), 7.89-7.77 (m, 5H), 7.61-7.53
(m, 2H), 7.45 (q, J=7.0Hz, 2H), 7.38-7.34 (m, 1H), 7.22 (s, 1H)；13C NMR (100MHz, CDCl3,
Ppm) δ 154.3,151.0,137.7,134.4,129.7,128.8,128.2,127.5,127.4,127.2,126.4,124.3,
124.1,120.7,120.5,119.3,113.4；HRMS calcd.for：C17H13N2S[M+H]+277.0794, found
277.0790.
The nuclear-magnetism and mass spectrometric data of 13 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.0Hz, 1H), 7.77 (d, J=8.0Hz, 1H), 7.57-
7.50 (m, 3H), 7.40 (t, J=7.4Hz, 1H), 7.24 (t, J=7.7Hz, 1H), 6.99 (s, 1H), 6.86 (d, J=
7.3Hz, 1H), 2.37 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.4,151.0,140.2,139.0,128.9,
128.1,127.1,124.1,123.2,120.7,120.4,118.7,115.2,21.6；HRMS calcd.for：C14H13N2S[M
+H]+241.0794 found 241.0790.
The nuclear-magnetism and mass spectrometric data of 14 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.1Hz, 1H), 7.78 (d, J=8.1Hz, 1H), 7.61-
7.49 (m, 3H), 7.41 (t, J=7.6Hz, 1H), 7.28 (t, J=7.8Hz, 1H), 7.01 (s, 1H), 6.90 (d, J=7.6,
1H), 2.68 (q, J=7.6Hz, 2H), 1.27 (t, J=7.6Hz, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.4,
151.0,145.4,140.2,129.0,128.1,127.1,124.1,121.9,120.7,120.4,117.6,115.5,29.0,
15.5；HRMS calcd.for：C15H15N2S[M+H]+255.0951 found 255.0949.
The nuclear-magnetism and mass spectrometric data of 15 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.93 (t, J=2.0Hz, 1H), 7.86 (d, J=8.1Hz, 1H), 7.78
(d, J=8.1Hz, 1H), 7.55 (t, J=7.6Hz, 2H), 7.44 (t, J=7.4Hz, 1H), 7.27 (tJ=6.5Hz, 1H),
7.09 (s, 1H), 7.01 (d, J=7.9,1H)；13C NMR (100MHz, CDCl3, ppm) and δ 153.7,151.0,141.4,
134.8,130.1,128.3,126.9,124.4,122.2,120.6,120.5,117.8,115.9；HRMS calcd.for：
C13H10ClN2S[M+H]+261.0248 found 261.0244.
The nuclear-magnetism and mass spectrometric data of 16 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 8.22 (d, J=8.0Hz, 1H), 7.84 (d, J=8.1Hz, 1H), 7.73
(d, J=8.1Hz, 1H), 7.54-7.50 (m, 1H), 7.40 (t, J=7.3Hz, 1H), 7.28-7.21 (m, 2H), 7.01 (t, J
=7.1Hz, 1H), 6.82 (s, 1H), 2.38 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.9,151.3,138.5,
130.5,128.1,127.2,127.0,126.5,124.2,122.9,120.9,120.5,119.7,17.7；HRMS
calcd.for：C14H13N2S[M+H]+241.0794 found 241.0795.
The nuclear-magnetism and mass spectrometric data of 17 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.95 (d, J=8.6Hz, 1H), 7.83 (d, J=8.1Hz, 1H), 7.72
(d, J=8.1Hz, 1H), 7.56-7.49 (m, 1H), 7.43-7.36 (m, 1H), 7.07-7.05 (m, 2H), 6.75 (s, 1H),
2.3 (s, 3H), 2.3 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 155.5,151.3,135.8,133.0,131.3,
128.1,127.7,127.5,127.0,124.1,121.0,120.8,120.5,20.8,17.7；HRMS calcd.for：
C15H15N2S[M+H]+255.0951 found 255.0948.
The nuclear-magnetism and mass spectrometric data of 18 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.84 (d, J=8.1Hz, 1H), 7.78 (d, J=8.1Hz, 1H), 7.55-
7.50 (m, 2H), 7.43-7.37 (m, 1H), 7.15 (dd, J=8.6,2.3Hz, 1H), 7.00 (s, 1H), 6.87 (d, J=
8.6Hz, 1H), 3.92 (s, 3H), 3.88 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ 155.0,150.9,149.2,
144.6,134.1,128.1,126.9,124.1,120.9,120.3,111.8,110.5,103.9,56.2,55.8；HRMS
calcd.for：C15H15N2O2S[M+H]+287.0849 found 287.0848.
The nuclear-magnetism and mass spectrometric data of 19 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.83 (dd, J=10.5,8.2Hz, 2H), 7.53 (t, J=7.4Hz,
1H), 7.40（T, J=7.7Hz, 1H), 7.08 (s, 3H), 3.88 (s, 6H), 3.83 (s, 3H)；13C NMR (100MHz, CDCl3,
Ppm) δ 154.5,153.5,150.9,136.6,133.2,128.2,127.0,124.2,120.8,120.4,96.1,61.0,
56.1；HRMS calcd.for：C16H17N2O3S[M+H]+317.0955 found 317.0954.
The nuclear-magnetism and mass spectrometric data of 20 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.76-7.68 (m, 2H), 7.63-7.54 (m, 2H), 7.34 (t, J=
7.9Hz, 2H), 7.18 (d, J=8.2Hz, 1H), 7.02 (t, J=7.4Hz, 1H), 6.96 (s, 1H), 2.47 (s, 3H)；13C
NMR (100MHz, CDCl3, ppm) and δ 154.2,151.4,140.3,138.7,129.1,126.0,125.2,122.1,120.3,
120.1,117.9,21.6；HRMS calcd.for：C14H13N2S[M+H]+241.0794 found 241.0794.
The nuclear-magnetism and mass spectrometric data of 21 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.77-7.72 (m, 2H), 7.61 (d, J=7.9Hz, 1H), 7.38-7.28
(m, 4H), 7.04 (t, J=7.4Hz, 1H), 7.00 (s, 1H), 2.53 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ
155.0,151.4,140.3,130.7,129.1,128.2,126.9,125.0,122.2,118.2,118.0,19.9；HRMS
calcd.for：C14H13N2S[M+H]+241.0794 found 241.0790.
The nuclear-magnetism and mass spectrometric data of 22 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.75-7.68 (m, 3H), 7.49 (dd, J=8.2,2.0Hz, 1H), 7.36
(t, J=7.9Hz, 2H), 7.14 (td, J=8.6,2.1Hz, 1H), 7.05 (t, J=7.4Hz, 1H), 6.96 (s, 1H)；13C
NMR (100MHz, CDCl3, ppm) and δ 162.8 (d, J=249.7Hz), 153.8,152.8 (d, J=10.2Hz), 140.0,
129.1,123.8,122.5,122.2 (d, J=10.2Hz), 118.2,113.5 (d, J=25.4Hz), 106.4 (d, J=
25.2Hz)；HRMS calcd.for：C13H10FN2S[M+H]+245.0543 found 245.0549.
The nuclear-magnetism and mass spectrometric data of 23 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.82 (d, J=1.6Hz, 1H), 7.72-7.67 (m, 3H), 7.39-7.34
(m, 3H), 7.08-7.04 (m, 1H), 7.00 (s, 1H)；13C NMR (100MHz, CDCl3, ppm) and δ 153.9,152.4,140.0,
135.1,129.2,125.6,125.1,122.6,121.6,120.0,118.1；HRMS calcd.for：C13H10ClN2S[M+H
]+261.0248 found 261.0245.
The nuclear-magnetism and mass spectrometric data of 24 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.96 (d, J=1.4Hz, 1H), 7.69 (dd, J=8.6,0.9Hz, 2H),
7.59 (d, J=8.6Hz, 1H), 7.48 (dd, J=8.6,1.6Hz, 1H), 7.38-7.33 (m, 2H), 7.05 (t, J=7.4Hz,
1H), 6.97 (s, 1H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.0,152.7,139.9,129.1,127.6,125.9,
123.3,123.0,122.5,121.7,118.1；HRMS calcd.for：C13H10BrN2S[M+H]+304.9743, found
304.9741.
The nuclear-magnetism and mass spectrometric data of 25 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.94 (d, J=1.3Hz, 1H), 7.72 (d, J=8.5Hz, 3H), 7.62
(dd, J=8.6,1.7Hz, 1H), 7.42-7.34 (m, 2H), 7.08 (t, J=7.4Hz, 1H), 6.97 (s, 1H)；13C NMR
(100MHz, CDCl3, ppm) and δ 153.4,149.9,139.9,131.3,129.2,128.7,123.7,122.6,121.7,
118.2,118.0；HRMS calcd.for：C13H10BrN2S[M+H]+304.9743 found 304.9747.
The nuclear-magnetism and mass spectrometric data of 26 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 8.05 (s, 1H), 7.94 (d, J=8.5Hz, 1H), 7.74 (dd, J=
8.6,1.0Hz, 3H), 7.42-7.34 (m, 2H), 7.13-7.01 (m, 2H)；13C NMR (100MHz, CDCl3, ppm) and δ 154.5,
154.3,139.8,129.2,126.9 (q, J=32.7Hz), 126.8,124.5 (q, J=2.8Hz), 124.1 (q, J=
270.6Hz), 122.8,121.1,118.4,118.3；HRMS calcd.for：C14H10F3N2S[M+H]+295.0512, found
295.0515.
The nuclear-magnetism and mass spectrometric data of 27 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 8.13 (s, 1H), 7.88 (d, J=8.4Hz, 1H), 7.73 (d, J=
8.4Hz, 2H), 7.63 (d, J=8.4Hz, 1H), 7.38 (t, J=7.6Hz, 2H), 7.09-7.05 (m, 2H)；13C NMR
(100MHz, CDCl3, ppm) and δ 154.1,151.2,139.8,130.3 (q, J=32.5Hz), 129.2,128.9,123.9 (q, J
=271.3Hz), 122.8,121.6,121.0 (q, J=3.2Hz), 118.2,117.9 (q, J=4.3Hz)；HRMS
calcd.for：C14H10F3N2S[M+H]+295.0512 found 295.0515.
The nuclear-magnetism and mass spectrometric data of 28 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.81 (d, J=8.2Hz, 1H), 7.71 (d, J=8.1Hz, 1H), 7.53-
7.48 (m, 1H), 7.38 (t, J=7.5Hz, 1H), 4.69 (s, 2H)；13C NMR (100MHz, CDCl3, ppm) and δ 158.6,
151.9,128.0,126.3,124.0,121.6,120.4；HRMS calcd.for：C7H7N2S[M+H]+151.0325, found
151.0321.
The nuclear-magnetism and mass spectrometric data of 29 product of embodiment are as follows：
1H NMR (400MHz, CDCl3, ppm) and δ 7.76 (d, J=8.2Hz, 1H), 7.38-7.31 (m, 3H), 7.22-7.14
(m, 3H), 7.04-7.00 (m, 1H), 6.91-6.88 (m, 1H), 3.60 (s, 3H)；13C NMR (100MHz, CDCl3, ppm) and δ
160.7,152.7,147.9,129.4,127.7,127.2,125.2,125.0,124.6,123.5,120.1,42.3；HRMS
calcd.for：C14H13N2S[M+H]+241.0794 found 241.0788.
Obviously, the above embodiments are merely examples for clarifying the description, and is not intended to limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And the obvious variation thus extended out or
Among changing still in the protection domain of the invention.
Claims (7)
1. a kind of 3- amino benzo [d] isothiazole and its derivative, its general formula is Formulas I：
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl.
A kind of 2. method for synthesizing 3- amino benzo [d] isothiazole and its derivative described in claim 1, which is characterized in that
It stirs to get benzenecarboximidamide class compound and elemental sulfur are heated under the reaction condition of inorganic base and organic solvent.
3. according to the method described in claim 2, it is characterized in that, the inorganic base is selected from KHCO3、K2CO3、Na2CO3、K3PO4、
K2HPO4、KOH、NaOH、Cs2CO3, potassium tert-butoxide, sodium tert-butoxide, sodium ethoxide, the one or more of sodium methoxide.
4. according to the method described in claim 2, it is characterized in that, the organic solvent be selected from pyridine, acetonitrile, THF, DMAC,
One or more in DMF, DMSO, Isosorbide-5-Nitrae-dioxane, toluene.
5. according to the method described in Claims 2 or 3 or 4, which is characterized in that the benzenecarboximidamide class compound, elemental sulfur, alkali
Molar ratio is 1: 3-5: 2-3, and reaction temperature is 110 DEG C -140 DEG C.
6. according to the method described in claim 2, it is characterized in that, the benzamidine compound be selected from C7-C19 fragrance amidines,
General formula is Formula II：
Wherein
R1 is selected from hydrogen atom, alkyl, halogen radical；
R2 is selected from hydrogen atom, alkyl；
R3 is selected from hydrogen atom；Substituted or non-substituted C6-C12 aryl；
X is selected from fluorine atom, chlorine atom, bromine atoms.
7. according to the method described in claim 6, it is characterized in that, the benzenecarboximidamide class compound in Formula II is selected from benzenecarboximidamide, 2-
Fluorobenzene carbonamidine, 2- chlordimeforms, 2- bromobenzene carbonamidines, the fluoro- N- phenyl benzenecarboximidamides of 2-, the chloro- N- phenyl benzenecarboximidamides of 2-, the bromo- N- benzene of 2-
Base benzenecarboximidamide, 2- chloro- N- (p-methylphenyl) benzenecarboximidamide, the chloro- N- of 2- (4- ethylphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- (tertiary butyl)
Phenyl) benzenecarboximidamide, the chloro- N- of 2- (4- methoxyphenyls) benzenecarboximidamide, the chloro- N- of 2- (4- ethoxyl phenenyls) benzenecarboximidamide, the chloro- N- of 2-
(4- Trifluoromethoxyphen-ls) benzenecarboximidamide, the chloro- N- of 2- (4- fluorophenyls) benzenecarboximidamide, the chloro- N- of 2- (4- chlorphenyls) benzenecarboximidamide, 2-
Chloro- N- (4- bromophenyls) benzenecarboximidamide, the chloro- N- of 2- ([1,1 '-biphenyl] -4- bases) benzenecarboximidamide, the chloro- N- of 2- (naphthalene -2- bases) benzenecarboximidamide,
The chloro- N- of 2- (m- tolyl) benzenecarboximidamide, the chloro- N- of 2- (m- ethylbenzene) benzenecarboximidamide, the chloro- N- of 2- (3- chlorphenyls) benzenecarboximidamide, 2-
Chloro- N- (o- tolyl) benzenecarboximidamide, the chloro- N- of 2- (2,4- 3,5-dimethylphenyl) benzenecarboximidamide, 2- chloro- N- (3,4- dimethoxy benzenes
Base) benzenecarboximidamide, the chloro- N- of 2- (3,4,5- trimethoxyphenyl) benzenecarboximidamide, the chloro- 4- Methyl-N-phenyls benzenecarboximidamides of 2-, the chloro- 3- of 2-
Methyl-N-phenyl benzenecarboximidamide, the fluoro- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the chloro- N- phenyl benzenecarboximidamides of the chloro- 4- of 2-, the bromo- N- of the chloro- 4- of 2-
Phenyl benzenecarboximidamide, the bromo- N- phenyl benzenecarboximidamides of the chloro- 5- of 2-, the chloro- 5- trifluoromethyls-N- phenyl benzenecarboximidamides of 2-, the chloro- 4- fluoroforms of 2-
Base-N- phenyl benzenecarboximidamides, 2- chloro-n-methyl-N- phenyl benzenecarboximidamides.
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| CN111304685A (en) * | 2019-03-08 | 2020-06-19 | 长沙理工大学 | Method for preparing 1,2,4-thiadiazole framework and fused rings thereof through electrocatalysis |
| CN113214182A (en) * | 2021-05-19 | 2021-08-06 | 佛山湘潭大学绿色智造研究院 | Benzisothiazole compound and preparation method thereof |
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| CN111304685A (en) * | 2019-03-08 | 2020-06-19 | 长沙理工大学 | Method for preparing 1,2,4-thiadiazole framework and fused rings thereof through electrocatalysis |
| CN111304685B (en) * | 2019-03-08 | 2021-10-08 | 长沙理工大学 | Method for preparing 1,2,4-thiadiazole framework and fused rings thereof through electrocatalysis |
| CN113214182A (en) * | 2021-05-19 | 2021-08-06 | 佛山湘潭大学绿色智造研究院 | Benzisothiazole compound and preparation method thereof |
| CN113214182B (en) * | 2021-05-19 | 2022-12-23 | 佛山湘潭大学绿色智造研究院 | Benzisothiazole compound and preparation method thereof |
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