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Synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds

A synthesis method and compound technology are applied in the field of synthesis of 6-hydroisoindolo[2,1-α]indole compounds, which can solve the problems of complicated synthesis steps and harsh conditions, and achieve simple and efficient reaction operations. High and universal effect

Active Publication Date: 2021-07-13
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are few related studies on the activation reaction of double carbon-hydrogen bonds in the molecule, and the synthesis of such compounds usually requires pre-functionalization, such as halogen, OTf and other groups on the benzene ring, and the synthesis steps are cumbersome and harsh.

Method used

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  • Synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds
  • Synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds
  • Synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Starting from 1a, a yellow solid was obtained Yield 93%.

[0058] 1 H NMR (400MHz, CDCl 3 )δ7.96(d,J=7.6Hz,1H),7.62(d,J=8.4Hz,1H),7.45-7.35(m,2H),7.33-7.27(m,2H),7.18(m,2H ),5.00(s,2H),3.17(s,6H).

[0059] 13 C NMR (101MHz, CDCl 3 )δ168.0, 144.70, 142.1, 133.1, 131.8, 130.2, 128.3, 128.0, 123.4, 123.2, 122.1, 121.4, 120.7, 109.6, 102.3, 48.5, 27.1.

[0060] HRMS (ESI) calcd for C 18 h 16 N 2 O(M+Na) + :299.1160,Found:299.1155.

Embodiment 2

[0062] Starting from 1b, a yellow solid was obtained Yield 93%.

[0063] 1 H NMR (400MHz, CDCl 3 )δ8.48(s,1H),7.98(d,J=7.6Hz,1H),7.60(d,J=7.2Hz,1H),7.48(d,J=7.7Hz,1H),7.29(d, J=6.5Hz,1H),7.17(m,2H),5.07(s,2H),3.94(s,3H),3.18(s,6H).

[0064] 13 C NMR (101MHz, CDCl 3 )δ167.5, 166.6, 146.6, 143.3, 133.0, 132.3, 130.6, 130.0, 129.3, 124.1, 123.2, 122.5, 121.6, 120.9, 109.6, 103.1, 77.2, 52.3, 48.6.

[0065] HRMS (ESI) calcd for C 20 h 18 N 2 o 3 (M+Na) + :357.1215,Found:357.1210.

Embodiment 3

[0067] Starting from 1c, a yellow solid was obtained Yield 82%.

[0068] 1 H NMR (400MHz, CDCl 3 )δ7.96(d, J=7.6Hz, 1H), 7.47-7.29(m, 4H), 7.05(d, J=7.5Hz, 1H), 6.94(d, J=7.1Hz, 1H), 5.33( s,2H),3.17(s,6H),2.71(s,3H).

[0069] 13 C NMR (101MHz, CDCl 3 )δ168.0, 144.7, 142.2, 132.8, 131.5, 130.3, 128.3, 127.8, 123.5, 123.2, 122.9, 120.8, 120.7, 119.0, 102.8, 77.2, 51.3, 17.8.

[0070] HRMS (ESI) calcd for C 19 h 18 N 2 O(M+H) + :313.1317,Found:313.1311.

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Abstract

The invention relates to a synthesis method of 6-hydroisoindolo[2,1-alpha]indole compounds, wherein the synthesis method comprises the steps: in an organic solvent system, synthesizing by taking a 1-aryl methylene indole compound as a basic raw material in the presence of a palladium catalyst, an oxidizing agent and an auxiliary additive, and post-treating the reaction liquid to obtain the 6-hydroisoindolo[2,1-alpha]indole compounds. According to the invention, starting from a 1-aryl methylene indole compound, in the presence of the palladium catalyst and the oxidizing agent, an intramolecular double-carbon hydrogen bond activation reaction is realized, and various 6-hydroisoindolo[2,1-alpha]indole compounds are synthesized at high yield. Indole raw materials which are simple and easy to synthesize and a catalytic amount of palladium are used in the reaction, the universality of a substrate is good, and the reaction operation is simple and convenient and high in efficiency. The obtained product can be used as a medical intermediate or a fluorescent luminescent material.

Description

technical field [0001] The invention relates to the technical field of synthesis of indole compounds, in particular to a synthesis method of 6-hydroisoindolo[2,1-α]indole compounds. Background technique [0002] Indole and its derivatives are a class of important heterocyclic compounds that are closely related to life activities. They are widely used in antihypertensive, antiviral, antitumor, analgesic, etc. They exist in many heterocyclic compounds with biological and medical applications. in ring compounds. Since many indole compounds have fluorescence, they can also be used as fluorescent materials. In recent years, there have been many catalytic synthesis methods for indole compounds, such as transition metal-catalyzed coupling reactions between indole and arene / alkane halides, transition metal-catalyzed intermolecular alkenylation reactions between indole and alkenes, and transition Metal-catalyzed arylation of indole with benzene, etc. [0003] However, there are fe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06B01J31/04
CPCC07D487/04C09K11/06B01J31/04C09K2211/1044C09K2211/1029
Inventor 段伟良谢士静
Owner YANGZHOU UNIV
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