An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives

被引：52
|
作者：
Alonso, Rafael [1 ]
Caballero, Alegria [1 ]
Campos, Pedro J. [1 ]
Sampedro, Diego [1 ]
Rodriguez, Miguel A. [1 ]
机构：
[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, Unidad Asociada CSIC, Logrono 26006, Spain
来源：
TETRAHEDRON | 2010年 / 66卷 / 25期
关键词：
Photochemistry; Oximes; Quinazolines; Theoretical calculations; THERMAL ELECTROCYCLIC REACTION; INTRAMOLECULAR CYCLOADDITION; RING-CLOSURE; QUINOLINE; 1-AZATRIENES; CYCLIZATION; ROUTE; PHOTOCYCLIZATION; IRRADIATION; ALKALOIDS;
D O I：
10.1016/j.tet.2010.04.082
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2). (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4469 / 4473
页数：5
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