CN108558885A - A kind of includes the synthetic method of the dihydro azepine of adjacent diaminophenazine structure and benzene-like compounds - Google Patents
A kind of includes the synthetic method of the dihydro azepine of adjacent diaminophenazine structure and benzene-like compounds Download PDFInfo
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- CN108558885A CN108558885A CN201810488167.5A CN201810488167A CN108558885A CN 108558885 A CN108558885 A CN 108558885A CN 201810488167 A CN201810488167 A CN 201810488167A CN 108558885 A CN108558885 A CN 108558885A
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- diaminophenazine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
The invention discloses the synthetic methods of a kind of dihydro azepine comprising adjacent diaminophenazine structure and benzene-like compounds, it is using hydrochloric acid as acidulant, NaCl is as solid supported agent, using diamino small molecule and adjacent aminophenazine class as raw material, 100 ~ 600 DEG C are heated to, 0.5 ~ 30min is reacted；Gained crude product is scattered in water or dilute sulfuric acid and boils after reaction, filters, washing, it is dry to get.The method of the present invention raw material is easy to get, and operating procedure is simple, green high-efficient：Without using organic solvent in reaction process, the reaction time only needs 0.5 ~ 30min；The yield of partial reaction is close to 100%.
Description
Technical field
The present invention relates to the synthetic methods of a kind of dihydro azepine and benzene and its derivative, more particularly to a kind of includes adjacent diamino
The dihydro azepine of base phenazine structure and the synthetic method of benzene and its derivative, belong to synthetic organic chemical art.
Background technology
Simultaneously benezene material is widely used in Organic Thin Film Transistors, Organic Light Emitting Diode, photovoltaic cell to four azepine of dihydro
Etc., therefore, exploitation is succinct, synthetic method efficiently, green is of great significance.Include the two of adjacent diaminophenazine structure
Simultaneously benzene and its derivative has following property to hydrogen azepine：Its fluorescent emission is located at yellow, red or near infrared region；Its solid has
There is higher field-effect mobility etc..It is mainly used in Organic Thin Film Transistors, Organic Light Emitting Diode, solar cell, dye
Send out agent, heterogeneous catalyst etc..Including the structural formula of the dihydro azepine acene of adjacent diaminophenazine structure is as follows：
Wherein, R1Selected from H or phenyl；R2Selected from H or methyl.Work as R1、R2When being selected from H, chemical name 5, dihydro -5 12-,
7,12,14- tetra- azepine pentacenes, DHTAP are its english abbreviations.Its structural formula is：
。
About four azepine pentacenes of 5,12- dihydros -5,7,12,14-（DHTAP）Synthesis have many reports：（1）By 4
Part diaminophenazine hydrochloride and 3 parts of o-phenylenediamine mixed grinding be placed in 170 DEG C of oil bath, then be brought rapidly up to
200-210 DEG C, 10-15min is kept, DHTAP is obtained（Berichte der deutschen chemischen
Gesellschaft, 1890, 23(2): 2789-2793.）.（2）By the diaminophenazine of 8g, 6g o-phenylenediamine and
The benzyl alcohol of 60c.c. is heated to reflux 14h, and the DHTAP of 7.8g can be obtained by post-processing.（3）By the adjacent benzene of oPD, 3.5g of 4.3g
After the mixing of the naphthalene of diamine hydrochloride and 60g, 20min is kept at 210-215 DEG C, the DHTAP of 0.75g is obtained by post-processing
（Journal of the Chemical Society, 1951: 3211-3215.）.（4）Dihydroxy benzoquinones（It is excessive）, adjacent benzene
Diamines and 6-methyl phosphonic triamide heat 12h at 150 DEG C, obtain DHTAP, yield 61%.（5）Dihydroxy benzoquinones（It is excessive）With
OPD, polyphosphoric acids heat 12h at 150 DEG C, obtain DHTAP, yield 98%（Macromolecules, 1968, 1(1):
36-42.）.（6）2, the 3- dihydroxyphenazines of 831mg, the o-phenylenediamine of 4.23g（It is 9 times excessive）After being mixed with 4ml benzyl alcohols
For 24 hours, the yield of gained DHTAP is 83% for 100 DEG C of heating（Organic Letters, 2008, 10(18): 4013-4016）.
（7）Dihydroxy benzoquinones, o-phenylenediamine and benzoic acid, are heated with heat gun, are kept 2min at 300 DEG C, are obtained DHTAP, yield 80%
（Langmuir, 2014, 30(20): 5700-5704.）.The synthesis of its corresponding derivative is similar.The above method exists such as
Next or multiple defects：Reaction time is long, and raw material availability is not high, and yield is relatively low, needs to use costly organic molten
Agent, operation is complicated, and post-processing is complicated.
Invention content
The purpose of the present invention is to provide a kind of raw material is cheap and easy to get, easy to operate, the reaction time is short, and synthetic yield is high
Include the synthetic method of adjacent diaminophenazine structure dihydro azepine acene class.
The method of dihydro azepine of the present invention synthesis comprising adjacent diaminophenazine structure and benzene-like compounds, is made with hydrochloric acid
For acidulant, NaCl is heated to 100 ~ 600 DEG C as solid supported agent, by raw material diamino small molecule and adjacent aminophenazine, instead
Answer 0.5 ~ 30min；Gained crude product is scattered in water or dilute sulfuric acid after reaction（It can accelerate washing process, quickly dissolve out
Impurity；A concentration of 0.001 ~ 2M）In boil, filter, washing, it is dry to get.
The diamino small molecule is o-phenylenediamine, N- methyl-o-phenylenediamines, N- phenyl o-phenylenediamine, 4,5- dimethyl-
12- phenylenediamines.
The adjacent aminophenazine be 2,3- diaminophenazines or 2- amino -3- hydroxyl azophenlyene, and diamino small molecule with
The molar ratio of adjacent diaminophenazine class is 1:0.1~1:10.
The amount of the acidulant hydrochloric acid is 1 ~ 100 times of diamino small molecule mole.
The amount of the solid supported agent NaCl is 0.1 ~ 100 times of diamino small molecule mole.
The synthetic product of the present invention is measured through nucleus magnetic hydrogen spectrum, consistent with target product.
The synthesis side of the present invention has the following advantages compared with the synthetic method having been reported：
1, raw material is easy to get：It is cheap and easy to get using adjacent diaminophenazine class as adminicle using diamino small molecule as raw material, it is at low cost；
2, operating procedure is simple：Only need to be by all raw materials and adminicle mixed once, grinding, directly heating can be complete in air
At reaction, filtered using simple washing, you can obtain product；Technical process is simple, easy to operate；
3, reaction condition is mild：Without solvent, it is not necessarily to inert gas shielding, reaction can be completed at 320 DEG C；
4, green high-efficient：Without using organic solvent in reaction process, the reaction time only needs 4 ~ 13min；The yield of partial reaction
Close to 100%.
Description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum of four azepine pentacenes of 5,12- dihydros -5,7,12,14-.
Fig. 2 is the nucleus magnetic hydrogen spectrum of four azepine pentacenes of 5- phenyl -12- hydrogen -5,7,12,14-.
Fig. 3 is the nucleus magnetic hydrogen spectrum of four azepine pentacenes of 2,3- dimethyl -5,12- dihydros -5,7,12,14-.
Specific implementation mode
The synthesis of dihydro azepine of the present invention and benzene and its derivative is described in detail below by specific embodiment.
Embodiment 1：The synthesis of four azepine pentacenes of 5,12- dihydros -5,7,12,14-
Take 51 mmol（3 g）NaCl, 0.5mmol（54 mg）O-phenylenediamine, the concentrated hydrochloric acid of 0.4ml grinds in grinding in alms bowl
It is extremely dry；It is then placed in the small crucible of 10ml, small crucible places into the big crucible of 50ml, closes the lid, in 320 DEG C of holdings
13min.Gained crude product, which is scattered in dilute sulfuric acid, to be boiled, and is filtered, and is washed, dry, obtains 32mg atropurpureus solids, and as 5,12-
Dihydro -5,7,12,14- tetra- azepine pentacenes, yield 67.8%.Its nucleus magnetic hydrogen spectrum is shown in Fig. 1.Reaction equation is as follows：
。
Embodiment 2：The synthesis of four azepine pentacenes of 5,12- dihydros -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.25mmol（52.5 mg）2,3- diaminophenazines, 0.3mmol（32.4 mg）It is adjacent
Phenylenediamine（Excessive 20%）In grinding in alms bowl, 150 μ L concentrated hydrochloric acids are added after mixing, are fully ground to dry；It is then charged into small test tube, in
320 DEG C of reaction 5min；Gained crude product, which is scattered in dilute sulfuric acid, to be boiled, and is filtered, and is washed, dry, obtains 76.4mg atropurpureus solids
As 5,12- dihydros -5,7,12,14- tetra- azepine pentacenes, yield 100%.Its nucleus magnetic hydrogen spectrum is shown in Fig. 1.Reaction equation is as follows：
。
Embodiment 3：The preparation of four azepine pentacenes of 5,12- dihydros -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.25mmol（52.8 mg）2- amino -3- hydroxyl azophenlyene, 0.3mmol（32.4 mg）
O-phenylenediamine（Excessive 20%）, add 150 μ L concentrated hydrochloric acids, be fully ground to dry, loading small test tube, 320 DEG C of reaction 5min.It will be thick
Product is scattered in dilute sulfuric acid and boils, and filtering, washing and drying obtains 76.4mg atropurpureus solids, as 5,12- dihydros -5,7, and 12,
Tetra- azepine pentacenes of 14-, yield 100%.Reaction equation is as follows：
。
Embodiment 4：The synthesis of four azepine pentacenes of 5,12- dihydros -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.25mmol（52.5 mg）2,3- diaminophenazines, 0.3mmol（58.5 mg）'s
N- methyl-o-phenylenediamine dihydrochlorides（Excessive 20%）In grinding in alms bowl, 150 μ L concentrated hydrochloric acids are added after mixing, are fully ground to dry；So
After be packed into small test tube, in 320 DEG C react 5min；Crude product be scattered in dilute sulfuric acid and boil, filter, wash, it is dry, obtain
55mg atropurpureus solids, as 5,12- dihydros -5,7,12,14- tetra- azepine pentacenes, yield 77%.Its nucleus magnetic hydrogen spectrum is shown in Fig. 1.
Reaction equation is as follows：
。
Embodiment 5：The synthesis of four azepine pentacenes of 5- phenyl -12- hydrogen -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.275mmol（57.8 mg）2,3- diaminophenazines（Excessive 10%）, 0.25mmo
（46.1 mg）N- phenyl o-phenylenediamine in grinding in alms bowl, after mixing plus 150 μ L concentrated hydrochloric acids, be fully ground to dry；It is then charged into
Small test tube reacts 5min in 320 DEG C；Gained crude product, which is scattered in dilute sulfuric acid, to be boiled, and is filtered, and is washed, dry, and it is black to obtain 70mg purples
Color solid, as 5- phenyl -12- hydrogen -5,7,12,14- tetra- azepine pentacenes, yield 78%.Its nucleus magnetic hydrogen spectrum is shown in Fig. 2.It is reacted
Formula is as follows：
。
Embodiment 6：The preparation of four azepine pentacenes of 5- phenyl -12- hydrogen -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.25mmol（52.8 mg）2- amino -3- hydroxyl azophenlyene, 0.3mmol（55.3 mg）
N- phenyl o-phenylenediamines（Excessive 20%）In grinding in alms bowl, 150 μ L concentrated hydrochloric acids are added after mixing, are fully ground to dry, loading lab scale
Pipe, 320 DEG C of reaction 5min.Crude product is scattered in dilute sulfuric acid and is boiled, is filtered, washing and drying obtains 72mg atropurpureus solid i.e.
For 5- phenyl -12- hydrogen -5,7,12,14- tetra- azepine pentacenes, yield 80%.Reaction equation is as follows：
。
Embodiment 7：The preparation of four azepine pentacenes of 8,9- dimethyl -5,12- dihydros -5,7,12,14-
Take 27mmol（1.6 g）NaCl, 0.25mmol（52.5 mg）2,3- diaminophenazines, 0.3mmol（40.9 mg）'s
4,5- dimethyl -1,2- phenylenediamines（Excessive 20%）In grinding in alms bowl, 150 μ L concentrated hydrochloric acids are added after mixing, are fully ground to dry, dress
Enter small test tube, 320 DEG C of reaction 5min.Crude product is scattered in dilute sulfuric acid and is boiled, is filtered, washing and drying obtains 75mg atropurpureus
Solid is 8,9- dimethyl -5,12- dihydros -5,7,12,14- tetra- azepine pentacenes, yield 96%.Reaction equation is as follows：
。
Embodiment 8：The preparation of four azepine pentacenes of 8,9- dimethyl -5,12- dihydros -5,7,12,14-
27mmol（1.6 g）NaCl, 0.25mmol（52.8 mg）2- amino -3- hydroxyl azophenlyene, 0.3mmol（40.9 mg）'s
4,5- dimethyl -1,2- phenylenediamines（Excessive 20%）In grinding in alms bowl, 150 μ L concentrated hydrochloric acids are added after mixing, are fully ground to dry, dress
Enter small test tube, 320 DEG C of reaction 5min.Crude product is scattered in dilute sulfuric acid and is boiled, is filtered, washing and drying obtains 74mg atropurpureus
Solid, yield 95%.Reaction equation is as follows：
。
Claims (8)
1. the synthetic method of a kind of dihydro azepine comprising adjacent diaminophenazine structure and benzene-like compounds, it is characterised in that：It is
Using hydrochloric acid as catalyst, NaCl is raw material as solid supported agent, diamino small molecule, is heated to 100 ~ 600 DEG C, reaction
0.5~30min；Gained crude product is scattered in water or dilute sulfuric acid and boils after reaction, filters, washing, it is dry to get.
2. the synthetic method of the dihydro azepine and benzene-like compounds as described in claim 1 comprising adjacent diaminophenazine structure,
It is characterized in that：The diamino small molecule is o-phenylenediamine, N- methyl-o-phenylenediamines, N- phenyl o-phenylenediamine, 4,5- dimethyl-
12- phenylenediamines.
3. the synthetic method of the dihydro azepine and benzene-like compounds as claimed in claim 1 or 2 comprising adjacent diaminophenazine structure,
It is characterized in that：Raw material further includes adjacent aminophenazine class.
4. the synthetic method of the dihydro azepine and benzene-like compounds as claimed in claim 3 comprising adjacent diaminophenazine structure,
It is characterized in that：Neighbour's aminophenazine class is 2,3- diaminophenazines or 2- amino -3- hydroxyl azophenlyene.
5. the synthetic method of the dihydro azepine and benzene-like compounds as claimed in claim 3 comprising adjacent diaminophenazine structure,
It is characterized in that：The molar ratio of the diamino small molecule and adjacent diaminophenazine class is 1:0.01~1:100.
6. the synthetic method of the dihydro azepine and benzene-like compounds as claimed in claim 3 containing adjacent diaminophenazine structure, special
Sign is：The amount of acidulant hydrochloric acid is 1 ~ 100 times of diamino small molecule mole.
7. the synthetic method of the dihydro azepine and benzene-like compounds as described in claim 1 comprising adjacent diaminophenazine structure,
It is characterized in that：The amount of solid supported agent NaCl is 0.1 ~ 100 times of diamino small molecule mole.
8. the synthetic method of the dihydro azepine and benzene-like compounds as described in claim 1 comprising adjacent diaminophenazine structure,
It is characterized in that：A concentration of 0.001 ~ 2M of the dilute sulfuric acid.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH469784A (en) * | 1965-10-20 | 1969-03-15 | Eastman Kodak Co | Process for preparing fluorindine compounds |
| GB1159130A (en) * | 1965-10-23 | 1969-07-23 | Eastman Kodak Co | Process for the Preparation of Fluorindine Dyes |
| SU595315A1 (en) * | 1975-07-25 | 1978-02-28 | Предприятие П/Я А-7850 | 2-aminophenazine derivatives as fluorescent colours and pigments for plastics |
| CN1958578A (en) * | 2006-11-09 | 2007-05-09 | 重庆医科大学 | Method for preparing dichloroquinoxaline, and nitro-derivative |
| WO2009083532A2 (en) * | 2007-12-28 | 2009-07-09 | Universite De La Mediterranee Aix-Marseille Ii | Novel method for the preparation of derivatives of dihydrotetraazapentacenes, products such as obtained, and uses thereof |
| CN102702242A (en) * | 2012-05-29 | 2012-10-03 | 天津理工大学 | Preparation and application of novel phenazine imidazo phenylboronic acid fluorescence sugar probe |
| US20130331572A1 (en) * | 2012-06-07 | 2013-12-12 | Signa S.A. De C.V. | Processes for the preparation of sodium 5,14-dihydrotetraazapentacene polysulfonate, and intermediates thereof |
| CN105481869A (en) * | 2015-12-04 | 2016-04-13 | 中国药科大学 | Pyrano [3,2-a] phenazine derivative, preparation method and application thereof |
| CN105936636A (en) * | 2016-05-06 | 2016-09-14 | 西北师范大学 | Preparation methods and application of long chain-containing phenazine derivative gel factor and metal gel thereof |
-
2018
- 2018-05-21 CN CN201810488167.5A patent/CN108558885A/en active Pending
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH469784A (en) * | 1965-10-20 | 1969-03-15 | Eastman Kodak Co | Process for preparing fluorindine compounds |
| GB1159130A (en) * | 1965-10-23 | 1969-07-23 | Eastman Kodak Co | Process for the Preparation of Fluorindine Dyes |
| SU595315A1 (en) * | 1975-07-25 | 1978-02-28 | Предприятие П/Я А-7850 | 2-aminophenazine derivatives as fluorescent colours and pigments for plastics |
| CN1958578A (en) * | 2006-11-09 | 2007-05-09 | 重庆医科大学 | Method for preparing dichloroquinoxaline, and nitro-derivative |
| WO2009083532A2 (en) * | 2007-12-28 | 2009-07-09 | Universite De La Mediterranee Aix-Marseille Ii | Novel method for the preparation of derivatives of dihydrotetraazapentacenes, products such as obtained, and uses thereof |
| CN102702242A (en) * | 2012-05-29 | 2012-10-03 | 天津理工大学 | Preparation and application of novel phenazine imidazo phenylboronic acid fluorescence sugar probe |
| US20130331572A1 (en) * | 2012-06-07 | 2013-12-12 | Signa S.A. De C.V. | Processes for the preparation of sodium 5,14-dihydrotetraazapentacene polysulfonate, and intermediates thereof |
| MX338113B (en) * | 2012-06-07 | 2016-04-01 | Signa S A De C V | Processes for the preparation of sodium 5,14-dihydrotetraazapenta cene polysulfonate, and intermediates thereof. |
| CN105481869A (en) * | 2015-12-04 | 2016-04-13 | 中国药科大学 | Pyrano [3,2-a] phenazine derivative, preparation method and application thereof |
| CN105936636A (en) * | 2016-05-06 | 2016-09-14 | 西北师范大学 | Preparation methods and application of long chain-containing phenazine derivative gel factor and metal gel thereof |
Non-Patent Citations (3)
| Title |
|---|
| OTTO FISCHER,ET AL.: "Ueber die Fluorindine", 《BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT》 * |
| 冯根锋: "二氢-5,7,12,14-四氮并五苯及其衍生物的合成研究", 《中国优秀硕士学位论文全文数据库 医药卫生科技辑》 * |
| 郭书好主编: "《有机化学实验》", 31 July 2006, 华中科技大学出版社 * |
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Application publication date: 20180921 |