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

Autor: Ksenia Malkova, Andrey Bubyrev, Stanislav Kalinin, Dmitry Dar’in
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 19, Iss 1, Pp 800-807 (2023)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.19.60
Popis: 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.
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