Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones

A domino aldol-S(N)Ar-dehydration [3+3] annulation strategy has been utilized to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides have been reacted with 2-fluorobenzaldehyde derivatives activated toward S(N)Ar reaction by an electron-withdrawing substituent (NO(2), CN, CF(3...

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Detalles Bibliográficos
Autores principales: Fobi, Kwabena, Ametsetor, Ebenezer, Bunce, Richard A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420682/
https://www.ncbi.nlm.nih.gov/pubmed/37570826
http://dx.doi.org/10.3390/molecules28155856
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author Fobi, Kwabena
Ametsetor, Ebenezer
Bunce, Richard A.
author_facet Fobi, Kwabena
Ametsetor, Ebenezer
Bunce, Richard A.
author_sort Fobi, Kwabena
collection PubMed
description A domino aldol-S(N)Ar-dehydration [3+3] annulation strategy has been utilized to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides have been reacted with 2-fluorobenzaldehyde derivatives activated toward S(N)Ar reaction by an electron-withdrawing substituent (NO(2), CN, CF(3), CO(2)Me) at C5 to prepare 3,6-disubstituted quinolin-2(1H)-ones. Additionally, 3-substituted 1,8-naphthyridin-2(1H)-ones have been similarly derived from 2-fluoronicotinaldehyde. Fifteen examples are reported, and two possible mechanistic scenarios are presented and discussed.
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spelling pubmed-104206822023-08-12 Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones Fobi, Kwabena Ametsetor, Ebenezer Bunce, Richard A. Molecules Article A domino aldol-S(N)Ar-dehydration [3+3] annulation strategy has been utilized to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides have been reacted with 2-fluorobenzaldehyde derivatives activated toward S(N)Ar reaction by an electron-withdrawing substituent (NO(2), CN, CF(3), CO(2)Me) at C5 to prepare 3,6-disubstituted quinolin-2(1H)-ones. Additionally, 3-substituted 1,8-naphthyridin-2(1H)-ones have been similarly derived from 2-fluoronicotinaldehyde. Fifteen examples are reported, and two possible mechanistic scenarios are presented and discussed. MDPI 2023-08-03 /pmc/articles/PMC10420682/ /pubmed/37570826 http://dx.doi.org/10.3390/molecules28155856 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Fobi, Kwabena
Ametsetor, Ebenezer
Bunce, Richard A.
Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title_full Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title_fullStr Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title_full_unstemmed Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title_short Domino Aldol-S(N)Ar-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
title_sort domino aldol-s(n)ar-dehydration sequence for [3+3] annulations to prepare quinolin-2(1h)-ones and 1,8-naphthyridin-2(1h)-ones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420682/
https://www.ncbi.nlm.nih.gov/pubmed/37570826
http://dx.doi.org/10.3390/molecules28155856
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