Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4

Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4

A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H(2)SO(4) (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cycl...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-08, Vol.10 (29), p.5643-5646
Hauptverfasser: Liu, Xu, Xin, Xin, Xiang, Dexuan, Zhang, Rui, Kumar, Santosh, Zhou, Fenguo, Dong, Dewen
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Amides - chemistry
Cyclization
Quinolones - chemical synthesis
Quinolones - chemistry
Stereoisomerism
Sulfuric Acids - chemistry
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Zusammenfassung:A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H(2)SO(4) (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cyclization reactions is proposed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25767j