An investigation of the allylation cascade reactions of substituted indigos

Perry, Matthew J., Willis, Anthony C., Bremner, John B., and Keller, Paul A. (2023) An investigation of the allylation cascade reactions of substituted indigos. RSC Advances, 13 (7). pp. 4865-4873.

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Abstract

In a continuation of the exploration of indigo cascade reactions, a series of –OMe, –Ph, –Br and –NO2 substituted indigos 1a–i were synthesised to probe electronic effects upon the outcome of allylation cascade reactions. When indigos 1a–i in the presence of base were reacted with allyl bromide, spiroindolinepyridoindolones 17–25 (36–75%) were obtained as the major products in each case, marking a shift in outcome relative to that previously reported for unsubstituted indigo. In electron-rich derivatives (–OMe, –Ph), C-allylspiroindolinepyridoindolediones 26–29 (3–11%) were also isolated, which are most likely formed via a Claisen rearrangement of the respective spiroindolinepyridoindolones 18–21. Additionally, the isolation of diallylbiindolone 16, oxazinobiindole 30 and N,N′-diallyl-3,3′-bis(allyloxy) biindole 31 each represented novel polyheterocyclic derivatives, providing intriguing new mechanistic insights, reaction pathways and in the case of 30 the first common heterocyclic skeletal outcome shared in both allylation and propargylation cascade reactions of indigo.

Item ID: 80598
Item Type: Article (Research - C1)
ISSN: 2046-2069
Copyright Information: © 2023 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a CC 3.0 Unported License.
Date Deposited: 02 Oct 2023 23:35
FoR Codes: 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 100%
SEO Codes: 28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280105 Expanding knowledge in the chemical sciences @ 100%
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