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

共 50 条

[1] An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
Gaso-Sokac, Dajana
Busic, Valentina
Cetina, Mario
Jukic, Marijana
MOLECULES, 2014, 19 (06) : 7610 - 7620
[2] INFRARED PHOTOCHEMISTRY OF FBRCO - AN EXPERIMENTAL AND THEORETICAL-STUDY
ZHAO, Y
FRANCISCO, JS
MOLECULAR PHYSICS, 1993, 79 (01) : 1 - 11
[3] Photochemistry of Salicylaldoxime in Solid Argon: An Experimental and Theoretical Study
Grzegorzek, Joanna
Mielke, Zofia
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (27) : 5301 - 5309
[4] Synthesis, QSAR Study and Optimization of Propiophenone Oxime Derivatives
Chen Liang
Huang Ying
Xie Wei
Cao Jin
Ni Changchun
Shen Zhou
Li Xiuli
Zhang Yibin
Shen Tianxiang
Yu Fei
Liu Bin
Yuan Liping
Yao Jianhua
CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (01) : 33 - 42
[5] Efficient Synthesis of Novel Pyranoquinoline Derivatives from Simple Acetanilide Derivatives: Experimental and Theoretical Study of their Physicochemical Properties using DFT Calculations
Mirjafary, Zohreh
Saidian, Hamid
Sahandi, Morteza
Shojaei, Leila
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2014, 25 (07) : 1253 - 1260
[6] Experimental and theoretical investigations of benzamide oxime
Arjunan, V.
Mythili, C. V.
Mageswari, K.
Mohan, S.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2011, 79 (01) : 245 - 253
[7] Experimental and theoretical study of hydrocarbon photochemistry applied to Titan stratosphere
Vuitton, V.
Doussin, J. -F.
Benilan, Y.
Raulin, F.
Gazeau, M. -C.
ICARUS, 2006, 185 (01) : 287 - 300
[8] Study on the Synthesis and Hypolipidemic Activities of Coumarin Oxime Esters Derivatives
Chang, Haoyun
Li, Guangyao
Liu, Peng
Hu, Supei
Huang, Peng
Hu, Haixia
Xu, Nongzhang
Zhou, Yang
INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2023, 57 (04) : 1159 - 1166
[9] THEORETICAL AND EXPERIMENTAL-STUDY ON THE SYNTHESIS OF N AND O SUBSTITUTED DERIVATIVES OF PYRROLIDONE
ONISCU, C
SURPATEANU, G
HOROBA, E
REVISTA DE CHIMIE, 1984, 35 (11): : 985 - 987
[10] Synthesis of New β-Carboline Derivatives Fused with β-Lactam Rings: An Experimental and Theoretical Study
Milen, Matyas
Abranyi-Balogh, Peter
Mucsi, Zoltan
Dancso, Andras
Frigyes, David
Pongo, Laszlo
Keglevich, Gyoergy
CURRENT ORGANIC CHEMISTRY, 2013, 17 (17) : 1894 - 1902

← 1 2 3 4 5 →