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

Autor:	Kwabena Fobi, Ebenezer Ametsetor, Richard A. Bunce
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	quinolin-2(1H)-ones 1 8-naphthyridin-2(1H)-ones heterocycle synthesis aldol-SNAr-dehydration reactions domino reactions [3+3] annulation Organic chemistry QD241-441
Zdroj:	Molecules, Vol 28, Iss 15, p 5856 (2023)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules28155856
Popis:	A domino aldol-SNAr-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 SNAr reaction by an electron-withdrawing substituent (NO2, CN, CF3, CO2Me) 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.
Databáze:	Directory of Open Access Journals
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