Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β -ketosulfonamides and sulfones

Abstract
Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields.

Beilstein J. Org. Chem. 2023, 19, 800–807. doi:10.3762/bjoc.19.60

Source: Beilstein Journal of Organic Chemistry - June 9, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aza-Wittig reaction azides cyclocondensation quinolones sulfonamides Full Research Paper Source Type: research