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

Autor: Khatoon, Rafia, Jandial, Tanvi, Gupta, Anish, Kundan, Sujata, Sridharan, Vellaisamy
Předmět:
Zdroj: Synthesis; Jan2025, Vol. 57 Issue 1, p218-228, 11p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index