One-Pot, Two-Step Synthesis of Highly Functionalized 4-Indolyl/Pyrrolyl-Chromanes via a para-Quinone Methide Formation–1,8-Addition Sequence

Abstract

An efficient one-pot, two-step synthesis of structurally diverse 4-indolyl-/pyrrolyl-chromanes was developed starting from o-propargylated salicylaldehydes, 2,6-dialkylphenols and indoles/pyrrole. This process begins with a sequential secondary amine-catalyzed formation of p-quinone methides followed by Brønsted acid catalyzed 1,8-addition with indoles/pyrrole to access the functionalized chromanes in high yields (up to 91%). This sequential reaction generates three new C–C bonds, shows high step- and atom-economy with only one molecule of water as the side product and gives access to complex molecular frameworks without the need for the isolation of the intermediates.

Key words

heterocycles - 4-indolyl-chromanes - 4-pyrrolyl-chromanes - p-quinone methide - 1,8-addition

Publication History

Received: 04 June 2024

Accepted after revision: 23 July 2024

Accepted Manuscript online:
23 July 2024

Article published online:
20 August 2024

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