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Preparation method for indole condensed seven-membered lactam compound

A technology of fusing a lactam compound and an indole is applied in the field of preparation of seven-membered lactam compounds, which can solve the problems of limited synthesis method, difficulty in forming a skeleton and the like, and achieve the effects of wide substrate adaptability, easy reaction and simple conditions.

Pending Publication Date: 2020-05-01
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 for indole condensed seven-membered lactam compound
  • Preparation method for indole condensed seven-membered lactam compound
  • Preparation method for indole condensed seven-membered lactam compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Into the Schlenk lock reactor, sequentially add the 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, the reaction is complete as monitored by TLC, and the reaction solution is concentrated 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),2.10–1.9...

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 for an indole condensed seven-membered lactam compound. The method prepares a series of indole condensed seven-membered lactam compounds by using an indolyl alkyne amide compound as a raw material in the presence of a zinc catalyst and an N-oxide oxidizing agent. The method has the following advantages: a noble metal catalyst is not needed; the reactionis easy to operate; the conditions are mild and simple; the substrate application range is wide; and the target product yield is medium to excellent.

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 seven-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 INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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