PPh3‑Mediated Cascade Reaction of 2‑Alkynylnitrobenzenes and Thioureas for the Construction of Imidazo[4,5‑b]indole-2-thiones

PPh3‑Mediated Cascade Reaction of 2‑Alkynylnitrobenzenes and Thioureas for the Construction of Imidazo[4,5‑b]indole-2-thiones

A simple method for the preparation of imidazo­[4,5-b]­indole-2-thiones from 2-alkynylnitrobenzenes and thioureas is described. In the reaction, a Wittig-like process was triggered by PPh3 and followed by a cyclization step. The products were afforded in yields of 70–98% under mild conditions. Addit...

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Veröffentlicht in:Journal of organic chemistry 2023-03, Vol.88 (5), p.2801-2808
Hauptverfasser: Xu, Yao, Fan, Hui, Yang, Fan, Xu, Shijie, Zhao, Xuechun, Liao, Xiaoming, Zhang, Xiaoxiang
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couplings
cyclization reactions
methodology
organic chemistry
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container_end_page 2808
container_issue 5
container_start_page 2801
container_title Journal of organic chemistry
container_volume 88
creator Xu, Yao
Fan, Hui
Yang, Fan
Xu, Shijie
Zhao, Xuechun
Liao, Xiaoming
Zhang, Xiaoxiang
description A simple method for the preparation of imidazo­[4,5-b]­indole-2-thiones from 2-alkynylnitrobenzenes and thioureas is described. In the reaction, a Wittig-like process was triggered by PPh3 and followed by a cyclization step. The products were afforded in yields of 70–98% under mild conditions. Additionally, the 2-alkynylnitrobenzenes were stable and could be prepared via a simple coupling step.
doi_str_mv 10.1021/acs.joc.2c02434
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subjects couplings
cyclization reactions
methodology
organic chemistry
title PPh3‑Mediated Cascade Reaction of 2‑Alkynylnitrobenzenes and Thioureas for the Construction of Imidazo[4,5‑b]indole-2-thiones
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