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

Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar -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 ,...

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Published in:RSC advances 2019-12, Vol.9 (71), p.4142-4148
Main Authors: Velezheva, V. S, Babii, O. L, Khodak, A. A, Alekseeva, E. A, Nelyubina, Yu V, Godovikov, I. A, Peregudov, A. S, Majorov, K. B, Nikonenko, B. V
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Summary:Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar -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. Based on hemiindigos we developed novel reactions for producing -carbolines and their precursors that appeared to be active against MTB.
ISSN:2046-2069
DOI:10.1039/c9ra07807j