Preparation method of indole condensed octatomic lactam compounds

A technology for the fusion of lactam compounds and indole, which is applied in organic chemistry and other fields, can solve the problems of limited synthesis methods and difficulty in forming a skeleton, and achieve the effects of wide substrate adaptability, easy reaction and high yield

Pending Publication Date: 2020-04-17
瑞安宝源化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is often difficult to form these backbones due to entropic effects and cross-ring interactions
To date, the reported synthetic methods are very limited and most are limited to noble metal catalyzed

Method used

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  • Preparation method of indole condensed octatomic lactam compounds
  • Preparation method of indole condensed octatomic lactam compounds
  • Preparation method of indole condensed octatomic lactam compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Into the Schlenk lock reactor, sequentially add additive NaBAr F 4 (0.04mmol, 35.6mg), the catalyst zinc trifluoromethanesulfonate (Zn(OTf) 2 ) (0.02mmol, 7.3mg), the indolyl alkyne amide compound (0.20mmol) shown in formula I-1 and the N-oxide oxidant (R=2,6-Cl 2 , 60.0mg, 0.4mmol), then add the organic solvent DCE (dichloroethane, 2mL), replace the reactor with a nitrogen atmosphere, heat and stir at 80°C for 0.5h, monitor the completion of the reaction by TLC, and concentrate the reaction solution The residue was obtained and separated by silica gel column chromatography (elution solvent: n-hexane / ethyl acetate) to obtain the indole-fused eight-membered lactam compound represented by formula III-1. Yield: 92%. White solid (mp 225-226°C). 1 H NMR (400MHz, CDCl 3)δ8.05(d,J=8.8Hz,1H),7.37–7.32(m,3H),7.31–7.26(m,1H),7.25–7.16(m,2H),7.11–7.06(m,1H) ,6.84(d,J=8.0Hz,1H),5.51(s,1H),4.11–3.98(m,1H),3.82–3.73(m,1H),3.51–3.23(m,5H),3.17(s ,3H),2.10–1.97(m,2H)...

Embodiment 2

[0036] The oxidizing agent (R=2-Br, 2equiv) shown in formula II, the reaction time is 12h, does not add auxiliary agent NaBAr F 4 , all the other conditions are the same as in Example 1, and the productive rate is 27%.

Embodiment 3

[0038] The oxidizing agent (R=2-Cl, 2equiv) shown in formula II, the reaction time is 12h, no additive NaBAr is added F 4 , all the other conditions are the same as in Example 1, and the productive rate is 35%.

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Abstract

The invention discloses a preparation method of indole condensed octatomic lactam compounds. According to the method, indolyl alkyne amide compounds are taken as a raw material, a series of indole condensed octatomic lactam compounds are prepared in the presence of a zinc catalyst and an N-oxide oxidizing agent, a noble metal catalyst is not needed, the reaction is easy to operate, the condition is mild and simple, the substrate application range is wide, and the target product yield is high.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a preparation method of an indole-fused eight-membered lactam compound. Background technique [0002] Medium-sized lactams, especially indole-fused medium-sized lactams, such as Paullone and its derivatives and Balasubramide, etc. (see formula 1 below), are important structural units found in a large number of natural products and bioactive molecules. However, it is often difficult to form these frameworks due to entropic effects and cross-loop interactions. To date, the reported synthetic methods are very limited, and most are limited to noble metal catalysis. Therefore, there is an urgent need to develop novel construction strategies, especially those with high efficiency and flexibility. [0003] Formula 1: [0004] [0005] In the past decade, the generation of putative α-oxogolden carotenoid intermediates via gold-catalyzed intermolecular N–O bo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 钱鹏程叶龙武
Owner 瑞安宝源化工有限公司
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