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

被引：1
|
作者：
Fobi, Kwabena [1 ]
Ametsetor, Ebenezer [1 ]
Bunce, Richard A. [1 ]
机构：
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
来源：
MOLECULES | 2023年 / 28卷 / 15期
关键词：
quinolin-2(1H)-ones; 1; 8-naphthyridin-2(1H)-ones; heterocycle synthesis; aldol-SNAr-dehydration reactions; domino reactions; 3+3] annulation; DERIVATIVES; DESIGN; ACCESS;
D O I：
10.3390/molecules28155856
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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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页数：12
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