Facile access to 3-sulfonyl quinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-keto sulfonamides and sulfones

Submitting author affiliation:
Saint Petersburg State University, Saint Petersburg, Russian Federation

Beilstein Arch. 2023, 202310. https://doi.org/10.3762/bxiv.2023.10.v1

Published 04 Apr 2023

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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 Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate both for ketosulfonyl reagents and α-sulfonyl alkyl acetates providing the target quinoline derivatives in good to excellent yields.

Keywords: quinolines, sulfonamides, cyclocondensation, aza-Wittig reaction, azides

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Malkova, K.; Bubyrev, A.; Kalinin, S.; Dar'in, D. Beilstein Arch. 2023, 202310. doi:10.3762/bxiv.2023.10.v1

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