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
相关论文
共 52 条
  • [1] Photocyclization of iminyl radicals:: Theoretical study and photochemical aspects
    Alonso, Rafael
    Campos, Pedro J.
    Rodriguez, Miguel A.
    Sampedro, Diego
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) : 2234 - 2239
  • [2] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines
    Alonso, Rafael
    Campos, Pedro J.
    Garcia, Barbara
    Rodriguez, Miguel A.
    [J]. ORGANIC LETTERS, 2006, 8 (16) : 3521 - 3523
  • [3] PHOTOCHEMICAL-SYNTHESIS OF QUINOLINE DERIVATIVES BY CYCLIZATION OF 4-ARYL-N-BENZOYLOXY-2,3-DIPHENYL-1-AZABUTA-1,3-DIENES
    ARMESTO, D
    GALLEGO, MG
    HORSPOOL, WM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (09): : 1623 - 1626
  • [4] BUCHI G, 1991, J ORG CHEM, V56, P2605
  • [5] Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines
    Campos, PJ
    Tan, CQ
    Rodriguez, MA
    Anon, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 7195 - 7197
  • [6] PHOTOCHEMISTRY OF 3-AMINO-2-ALKENIMINES - SYNTHESIS OF SUBSTITUTED QUINOLINES
    CAMPOS, PJ
    TAN, CQ
    GONZALEZ, JM
    RODRIGUEZ, MA
    [J]. TETRAHEDRON LETTERS, 1993, 34 (33) : 5321 - 5324
  • [7] CAMPOS PJ, 1994, SYNTHESIS-STUTTGART, P1155
  • [8] Synthesis of isoquinolines by irradiation of 1-methoxy-2-azabuta-1,3-dienes in a neutral medium
    Campos, PJ
    Caro, M
    Rodríguez, MA
    [J]. TETRAHEDRON LETTERS, 2001, 42 (21) : 3575 - 3577
  • [9] Choshi T, 2000, CHEM PHARM BULL, V48, P108
  • [10] NOVEL PHOTOCHEMICAL AND THERMAL ELECTROCYCLIZATION TO FUSED QUINOLINES
    ELFERINK, VHM
    BOS, HJT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (13) : 882 - 883
123456