Selective addition of Wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl(2-benzothiazolyl)acrylonitrile with some phosphorus ylides

被引:16
作者
Abdou, WM [1 ]
Ganoub, NAF [1 ]
Shaddy, AAM [1 ]
机构
[1] Natl Res Ctr, Cairo, Egypt
关键词
D O I
10.1016/S0040-4020(98)00545-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The behaviour of the acrylonitrile 1 toward different types of phosphorus ylides such as alkoxycarbonyl- 2a,b and beta-keto-alkylidene phosphoranes 2c-e as well as arylidenephosphorane 3 has been studied. The reactions take different pathways leading to unusual products, depending only oil the nature of the substituents of ylides used. All reactions proceed only in the presence of a base whereby a variety of 1,3-benzothiazalyl-[1,2-x] fused compounds, e.g. 6, 16 and 18: cyclopropene- 15 and cycloproprene- 19 derivatives as well as different types of new ylides: 7, 10 and 12a,b were isolated and established on chemical and physical evidence. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9079 / 9088
页数:10
相关论文
共 25 条
[1]  
ABDOU WM, 1991, CHEM IND-LONDON, P217
[2]   Comparative chemical studies of the behavior of 4-cyano-1,2-dithioles in analogy with 1,2,4-dithiazoles toward stable phosphonium ylides [J].
Abdou, WM ;
Ganoub, NAF .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 105 (1-4) :63-71
[3]   Reaction of N-phenyl-3,5-di-tert-butyl-1,2-benzoquinone monohydrazone and some phosphorus ylides [J].
Abdou, WM .
SYNTHETIC COMMUNICATIONS, 1997, 27 (20) :3599-3604
[4]   Reactions of alkylidenephosphoranes with symmetrically substituted p-quinones [J].
Abdou, WM ;
Salem, MAE ;
Sediek, AA .
TETRAHEDRON, 1997, 53 (40) :13945-13958
[5]  
Abdou WM, 1997, HETEROCYCL COMMUN, V3, P57
[6]   WITTIG REACTION OF 1-DICYANOMETHYLENEACENAPHTHEN-2-ONE [J].
ABDOU, WM ;
GANOUB, NAF .
HETEROATOM CHEMISTRY, 1992, 3 (02) :133-137
[7]  
ABDOU WM, 1995, HETEROCYCLIC COMM, V1, P387
[8]  
[Anonymous], 1965, ANGEW CHEM
[9]  
CADOGAN JIG, 1979, ORGANOPHOSPHORUS REA, pCH4
[10]   UNCATALYZED KNOEVENAGEL CONDENSATION OF 2-CYANOMETHYLBENZOTHIAZOLE WITH AROMATIC-ALDEHYDES - PREPARATION OF 3-ARYL-2-(2-BENZOTHIAZOLYL)ACRYLONITRILES AND 3-(2-BENZOTHIAZOLYL)COUMARIN IMINES [J].
DRYANSKA, V .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 61 (3-4) :325-329