Efficient allylation of 4-silyloxyquinolinium triflates and other positively charged heteroaromatic systems

被引:17
作者
Beifuss, U
Schniske, U
Feder, G
机构
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
[2] Univ Bayreuth, Organ Chem Lab, D-95447 Bayreuth, Germany
关键词
allylation; quinolines; benzopyrans; sulfur heterocycles; tin and compounds; silicon and compounds;
D O I
10.1016/S0040-4020(00)01066-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective allylation of 4-silyloxyquinolinium triflates with allyltri-n-butyltin has been performed to give 2-allyl-4-silyloxy-1,2-dihydroquinolines with excellent yields. Similiar results have been obtained with 4-silyloxy-l-benzopyrylium triflates and 4-silyloxy-1-benzothiopyrylium triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1005 / 1013
页数:9
相关论文
共 30 条
  • [1] Beifuss U, 1997, SYNLETT, P313
  • [2] 2-aminobuta-1,3-dienes as annulation reagents for 4-quinolones and benzothiopyran-4-ones: an attractive route for the highly diastereoselective synthesis of acridine- and thioxanthene-derivatives
    Beifuss, U
    Taraschewski, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (19): : 2807 - 2809
  • [3] BEIFUSS U, 1995, ANGEW CHEM INT EDIT, V34, P647, DOI 10.1002/anie.199506471
  • [4] BEIFUSS U, 1994, PHOSPHORUS SULFUR, V95-6, P339
  • [5] BEIFUSS U, 1995, SYNLETT, P938
  • [6] Beifuss U, 1996, SYNLETT, P182
  • [7] Beifuss U, 1998, SYNLETT, P649
  • [8] BEIFUSS U, 1996, ORGANOSILICON CHEM, V2, P225
  • [9] BEIFUSS U, 1996, ORGANOSILICON CHEM, V2, P219
  • [10] Brocherieux-Lanoy S, 1999, SYNLETT, P405