Issue 71, 2019

Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles

Abstract

Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar γ-carbolines 2 that contain a carboxylate group and their two pentacyclic precursors 6, 7 from hemiindigos 1. The nucleophilic and pro-electrophilic chemistry described is new to the hemiindigos 1, and it led to the discovery of antimycobacterial scaffold characteristic of rimino-type pentacycles 6, 7 and potent drug clofazimine. The new scaffold like clofazimine appears to be useful in developing lead agents active against drug-resistant/dormant TB.

Graphical abstract: Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles

Supplementary files

Article information

Article type
Paper
Submitted
25 ก.ย. 2562
Accepted
04 ธ.ค. 2562
First published
13 ธ.ค. 2562
This article is Open Access
Creative Commons BY license

RSC Adv., 2019,9, 41402-41408

Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles

V. S. Velezheva, O. L. Babii, A. A. Khodak, E. A. Alekseeva, Y. V. Nelyubina, I. A. Godovikov, A. S. Peregudov, K. B. Majorov and B. V. Nikonenko, RSC Adv., 2019, 9, 41402 DOI: 10.1039/C9RA07807J

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