Scaffold-divergent synthesis of ring-fused indoles, quinolines, and quinolones via iodonium-induced reaction cascades

Rosliana Halim, Luigi Aurelio, Peter John Scammells, Bernard Luke Flynn

Research output: Contribution to journalArticleResearchpeer-review

26 Citations (Scopus)

Abstract

N-(2-lodophenyl)imines A are readily formed from Schiff s base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.
Original languageEnglish
Pages (from-to)4708 - 4718
Number of pages11
JournalThe Journal of Organic Chemistry
Volume78
Issue number10
DOIs
Publication statusPublished - 2013

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