Rh-III-Catalyzed formal [5+1] cyclization of 2-pyrrolyl/indolylanilines using vinylene carbonate as a C1 synthon

A rhodium(iii)-catalyzed formal C-H [5 + 1] cyclization of 2-pyrrolyl/indolylanilines with vinylene carbonate has been explored towards the potent assembly of diverse 4-methylpyrrolo[1,2-a]quinoxalines. This established protocol is characterized by an exceedingly simple reaction system, and excellen...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 8; pp. 1764 - 1769
Main Authors Nan, Jiang, Ma, Qiong, Yin, Jiacheng, Liang, Chengyuan, Tian, Lei, Ma, Yangmin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.04.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METAL-FREE SYNTHESIS
ROUTE
ACTIVATION
AMINATION
ANNULATION
ANILINES
EFFICIENT SYNTHESIS
QUINOLINES
C(SP)-H
ALKENYLATION
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Summary:A rhodium(iii)-catalyzed formal C-H [5 + 1] cyclization of 2-pyrrolyl/indolylanilines with vinylene carbonate has been explored towards the potent assembly of diverse 4-methylpyrrolo[1,2-a]quinoxalines. This established protocol is characterized by an exceedingly simple reaction system, and excellent functional group toleration and yields. Most importantly, entirely distinct from documented [4 + 2] cyclization conversions, herein, the emerging vinylene carbonate firstly presents as a C1 synthon to realize [5 + 1] annulation and shows new chemical reactivity. Biological studies indicate that these prepared products are promising candidates in terms of their antibacterial activity.
ISSN:2052-4129
DOI:10.1039/d1qo00040c