Synthesis method of polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds

A synthesis method and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of medium yield and low substrate universality, and achieve excellent yield, low production cost, The effect of mild reaction conditions

Active Publication Date: 2018-07-27
JIAXING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the substrate universality is not very wide, the yield is medium, and the toxic carbon monoxide atmosphere is used, which has certain risks

Method used

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  • Synthesis method of polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds
  • Synthesis method of polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds
  • Synthesis method of polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] Add N-Ts-8-p-chlorophenylnaphthylamine (0.1mmol), p-bromodiphenyl disulfide (0.06mmol), iodine (0.03mmol), PdCl 2 (0.01mmol) and DMSO (2ml), then stirred the reaction in an oil bath at 80°C until the reaction of N-Ts-8-p-chlorophenylnaphthylamine was complete. After the reaction, cool to room temperature, add water 10 times the volume of the solvent, and then extract 2-4 times with dichloromethane; combine the filtrate to remove the solvent by distillation under reduced pressure; separate through silica gel chromatography column, and distill under reduced pressure to obtain the product , the yield was 82%. The identification result is:

[0052] 1 H NMR (400MHz, CDCl 3 )δ8.42(d,J=7.3Hz,1H),7.75–7.70(m,2H),7.69(dd,J=6.2,1.8Hz,1H),7.64(d,J=8.1Hz,1H), 7.53(d,J=6.2Hz,2H),7.46–7.41(m,1H),7.25–7.16(m,6H),7.09–6.99(m,2H),6.84(d,J=8.1Hz,2H) ,2.14(s,3H). 13 C NMR (100MHz, CDCl 3)δ144.50,140.48,140.44,137.68,133.92,133.85,133.08,132.99,132.35,132.31,131.44,130.9...

Embodiment 2

[0054]

[0055] Add N-Ms-8-p-chlorophenylnaphthylamine (0.3mmol), diphenyl disulfide (0.18mmol), iodine (0.09mmol), Pd(TFA) in turn in a round bottom flask at room temperature 2 (0.06mmol) and DMF (4ml), then stirred the reaction in an oil bath at 70°C until the reaction of N-Ms-8-p-chlorophenylnaphthylamine was complete. After the reaction, cool to room temperature, add water 10 times the volume of the solvent, and then extract 2-4 times with dichloromethane; combine the filtrate to remove the solvent by distillation under reduced pressure; separate through silica gel chromatography column, and distill under reduced pressure to obtain the product , the yield was 75%. The identification result is:

[0056] yellow solid

[0057] 1 H NMR (400MHz, CDCl 3 )δ8.64(d, J=7.3Hz, 1H), 7.83(d, J=8.1Hz, 1H), 7.69(d, J=8.0Hz, 3H), 7.67–7.62(m, 1H), 7.59( d, J=3.7Hz, 2H), 7.24(t, J=8.3Hz, 4H), 7.15–7.06(m, 3H), 2.39(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ140.63,139.37,138.28,134.41,13...

Embodiment 3

[0059]

[0060] Add N-Ms-8-p-methylphenylnaphthylamine (0.5mmol), p-bromodiphenyl disulfide (0.3mmol), iodine (0.15mmol), Pd(OAc) in the reaction flask in turn at room temperature 2 (0.15mmol) and DMA (6ml), then stirred the reaction in an oil bath at 100°C until the reaction of N-Ms-8-p-methylphenylnaphthylamine was complete. After the reaction, cool to room temperature, add water 10 times the volume of the solvent, and then extract 2-4 times with dichloromethane; combine the filtrate to remove the solvent by distillation under reduced pressure; separate through silica gel chromatography column, and distill under reduced pressure to obtain the product , the yield was 65%. The identification result is:

[0061] yellow solid

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.55(d, J=7.3Hz, 1H), 7.81(d, J=8.2Hz, 1H), 7.67(d, J=7.5Hz, 1H), 7.62(t, J=7.8Hz, 3H) ,7.57(d,J=7.8Hz,2H),7.23(d,J=8.5Hz,2H),7.15–7.14(m,1H),7.14–7.05(m,3H),2.38(s,3H), 2.30(s,3H). 13 C NMR (100MHz, CDCl 3 )δ14...

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Abstract

The invention discloses a synthesis method of polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds. Firstly, 8-alkynylnaphthylamine compounds, thioether (diselenide), acatalyst and an additive are placed in a reactor, a solvent is added to the reactor until 8-alkynylnaphthylamine compounds and thioether (diselenide) are completely dissolved, then, the mixture is heated to react, after the reaction, aftertreatment is performed, and the polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds are obtained. The polysubstituted sulfur-containing or selenium-containing benzo[c,d]indole compounds are synthesized with a one-pot one-step method, the reaction operation is simple, intermediate separation and purification processes are reduced, the reaction condition is mild, the reaction selectivity is good, the yield is high, the substrate universality is wide, the reaction materials are simple and easy to obtain, the production cost islow, and the method is applicable to large-scale industrial production as well as small-scale laboratory preparation.

Description

technical field [0001] The present invention relates to a method for synthesizing a novel multi-substituted benzo[c,d]indole compound, in particular to the synthesis of a multi-substituted sulfur- or selenium-containing benzo[c,d]indole compound method. Background technique [0002] Aryl sulfides are an important class of functional molecules, and are important intermediates in drug synthesis and material synthesis. For example, the kinase inhibitor axitinib is a recently FDA-approved diaryl sulfide. In addition, 3-thioindole compounds are also an important class of sulfur-containing compounds, which have potential application value in anti-tumor, anti-HIV, and treatment of heart disease (Adv.Synth.Catal.2009,351,2615- 2618). [0003] Organic selenide is also a very effective anticancer active drug. It is particularly important to develop a new type of anticancer active drug under the situation that the incidence and mortality of cancer in my country are on the rise. Acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/90C07D405/12C09K11/06
CPCC07D209/90C07D405/12C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1088
Inventor 张莲鹏邱观音生姚金忠周宏伟
Owner JIAXING UNIV
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