Synthesis of Quinolines from 3-Formylchromone

A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible...

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Veröffentlicht in:	Journal of organic chemistry 2008-08, Vol.73 (15), p.6010-6013
Hauptverfasser:	Plaskon, Andrey S, Ryabukhin, Sergey V, Volochnyuk, Dmitriy M, Gavrilenko, Konstantin S, Shivanyuk, Alexander N, Tolmachev, Andrey A
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Chromones - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Molecular Structure Organic chemistry Preparations and properties Quinolines - chemical synthesis Quinolines - chemistry Reactivity and mechanisms
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Beschreibung
Zusammenfassung:	A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible mechanism for the heterocyclizations was proposed.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo800950y