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

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 condensatio...

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Autores principales: Malkova, Ksenia, Bubyrev, Andrey, Kalinin, Stanislav, Dar’in, Dmitry
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10280061/
https://www.ncbi.nlm.nih.gov/pubmed/37346493
http://dx.doi.org/10.3762/bjoc.19.60
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author Malkova, Ksenia
Bubyrev, Andrey
Kalinin, Stanislav
Dar’in, Dmitry
author_facet Malkova, Ksenia
Bubyrev, Andrey
Kalinin, Stanislav
Dar’in, Dmitry
author_sort Malkova, Ksenia
collection PubMed
description 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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spelling pubmed-102800612023-06-21 Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones Malkova, Ksenia Bubyrev, Andrey Kalinin, Stanislav Dar’in, Dmitry Beilstein J Org Chem Full Research Paper 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-Institut 2023-06-09 /pmc/articles/PMC10280061/ /pubmed/37346493 http://dx.doi.org/10.3762/bjoc.19.60 Text en Copyright © 2023, Malkova et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Malkova, Ksenia
Bubyrev, Andrey
Kalinin, Stanislav
Dar’in, Dmitry
Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title_full Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title_fullStr Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title_full_unstemmed Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title_short Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
title_sort facile access to 3-sulfonylquinolines via knoevenagel condensation/aza-wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10280061/
https://www.ncbi.nlm.nih.gov/pubmed/37346493
http://dx.doi.org/10.3762/bjoc.19.60
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