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

页码：4469 / 4473

页数：5