期刊
MOLECULES
卷 28, 期 15, 页码 -出版社
MDPI
DOI: 10.3390/molecules28155856
关键词
quinolin-2(1H)-ones; 1; 8-naphthyridin-2(1H)-ones; heterocycle synthesis; aldol-SNAr-dehydration reactions; domino reactions; [3+3] annulation
A domino aldol-SNAr-dehydration [3+3] annulation strategy is used to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides are 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. Similarly, 3-substituted 1,8-naphthyridin-2(1H)-ones are derived from 2-fluoronicotinaldehyde. Fifteen examples are reported, and two possible mechanistic scenarios are presented and discussed.
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.
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