Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesis of 1,2,3,4,5,9-substituted benzazepine compound

A technology of benzazepine and synthesis method, which is applied in the field of organic compound process application, can solve problems such as no synthesis method proposed, and achieve the effects of promoting deep-level expansion, stable properties, and less stringent storage conditions

Inactive Publication Date: 2015-01-14
EAST CHINA NORMAL UNIV +1
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the construction of benzo five-membered nitrogen ring and benzo six-membered nitrogen ring has been realized in the prior art, as shown in formula (A), but the direct synthesis of benzo seven-membered nitrogen ring by Pd-catalyzed oxidative cyclization is still a challenge , no relevant synthetic method has been proposed in the prior art

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesis of 1,2,3,4,5,9-substituted benzazepine compound
  • Method for synthesis of 1,2,3,4,5,9-substituted benzazepine compound
  • Method for synthesis of 1,2,3,4,5,9-substituted benzazepine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Under the protection of inert gas, isatin compound 1a (0.2mmol) and alkyne compound 2a (1.0mmol) were dissolved in acetonitrile / 1,4-dioxane (2mL) (v / v=1:1), Add palladium acetate (0.02mmol) and silver acetate (0.4mmol), and stir the reaction system at 100°C for 12 hours, and detect it by TLC. After the reaction, cool down to room temperature, extract several times with dichloromethane, combine the organic phases, dry, and rotate The crude product was obtained by removing the solvent, and the product 3aa was obtained by flash column chromatography with a yield of 81%. 1 H NMR (300MHz, CDCl 3 ): δ=7.56(dd, J=7.3, 1.2Hz, 1H), 7.23-6.92(m, 18H), 6.79-6.75(m, 4H); 13 C NMR (75MHz, CDCl 3 ):δ=181.83,161.85,160.11,145.38,141.57,140.51,140.24,139.62,138.22,137.25,135.87,131.39,130.79,130.76,130.67,130.42,128.39,128.27,128.19,127.58,127.48,127.07,126.86, 126.27, 124.68, 121.71; HRMS (ESI) calculated value C 36 h 24 NO 2 [M+H] + 502.1802, actual value 502.1801....

Embodiment 2

[0026]

[0027] The operating steps are the same as in Example 1, and the yield is 96%. 1 H NMR (500MHz, CDCl 3 ): δ=7.37(s, 1H), 7.13-6.87(m, 17H), 6.72(m, 4H), 2.24(s, 3H); 13 C NMR (125MHz, CDCl3 ):δ=182.03,162.12,158.11,145.26,142.09,140.59,140.49,140.37,139.55,138.33,136.91,136.23,135.88,131.42,130.77, 130.70,130.53,130.41,128.34,128.24,128.14,127.55,127.44, 127.41, 127.01, 126.79, 124.93, 121.79, 21.30; HRMS (ESI) calculated value C 37 h 26 NO 2 [M+H] + 516.1958, actual value 516.1965.

Embodiment 3

[0029]

[0030] The operating steps are the same as in Example 1, and the yield is 93%. 1H NMR (500MHz, CDCl3): δ=7.42(t, J=9.9Hz, 1H), 7.13-6.90(m, 17H), 6.79-6.72(m, 4H), 2.76(hept, J=6.9Hz, 1H ), 1.14 (d, J=6.9Hz, 6H); 13C NMR (125MHz, CDCl3): δ=182.14, 162.05, 158.30, 147.15, 145.00, 140.57, 140.42, 140.39, 139.71, 138.36, 136.90, 135.90, 131. 130.79,130.75,130.63,130.43,128.25,128.21,128.11,127.53,127.43,127.40,127.00,126.79,122.29,121.69,33.84,23.91;HRMS(ESI)计算值C39H30NO2[M+H]+544.2271,实际值544.2286 ..

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesis of a 1,2,3,4,5,9-substituted benzazepine compound. The method comprises that an isatin compound and a disubstituted acetylene compound as raw materials undergo a reaction in one or more reaction solvents in the presence of a palladium catalyst and an oxidant in a nitrogen protective atmosphere to produce the 1,2,3,4,5,9-substituted benzazepine compound. The method adopts the easily available raw materials and has a simple synthesis route and high atom economical efficiency.

Description

technical field [0001] The invention specifically relates to a method for synthesizing 1,2,3,4,5,9-substituted benzazepine compounds, which belongs to the technical field of organic compound technology application. Background technique [0002] In recent years, chemists have been looking for greener organic synthesis methods. C-H bond activation has attracted the attention of many chemists due to its excellent characteristics in environmental friendliness and sustainability. This method realizes the Pd-catalyzed C-H / The N-H bond is broken, and the oxidative cycloaddition to the alkyne compound is completed to construct the nitrogen-containing heterocyclic compound. This kind of method has high atom economy and short steps. At present, the construction of benzo five-membered nitrogen ring and benzo six-membered nitrogen ring has been realized in the prior art, as shown in formula (A), but the direct synthesis of benzo seven-membered nitrogen ring by Pd-catalyzed oxidative cy...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C07F7/10
Inventor 姜雪峰汪舰李一鸣黄家尧李文军
Owner EAST CHINA NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com