β′-乙酰氧基Allenoates的发散[4+3]环：Azepino[1,2-a]吲哚衍生物的获取。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-14 DOI:10.1021/acs.joc.5c01904

Yannan Zhu,You Huang

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引用次数: 0

摘要

本文报道了Lewis碱催化的β′-乙酰氧基异丙酸酯与两种不同吲哚衍生物的发散[4 + 3]环化反应。采用DABCO催化剂，以2-（（3-甲酰基- 1h -吲哚-2-基）甲基）丙二酸盐为原料，顺利地合成了多种氮杂氮[1,2- A]吲哚衍生物。以3-甲酰基- 1h -吲哚-2-羧酰胺为原料，分别以DABCO和有机膦为催化剂合成了两个具有区域选择性的二氮杂基[1,2-a]吲哚衍生物。在三个1,2-熔融的七元吲哚产物中可以实现一系列官能团变换。

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Divergent [4+3] Annulations of β'-Acetoxy Allenoates: Access to Azepino[1,2-a]indole Derivatives.

In this work, the Lewis base-catalyzed divergent [4 + 3] annulation reactions of β'-acetoxy allenoates with two different indole derivatives are reported. A wide range of azepino[1,2-a]indole derivatives was smoothly obtained from 2-((3-formyl-1H-indol-2-yl)methyl)malonates by employing the DABCO catalyst. The syntheses of two regioselective diazepino[1,2-a]indole derivatives from 3-formyl-1H-indole-2-carboxamides are realized by the catalysis of DABCO and organophosphine, respectively. A series of functional group transformations can be achieved in the three 1,2-fused seven-membered indole products.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.