AZA WITTIG-TYPE REACTION BETWEEN THE IMINOPHOSPHORANE DERIVED FROM 3-AMINO-4-PHENYLTHIAZOLE-2(3H)-THIONE AND ISO(THIO)CYANATES - PREPARATION OF MESOIONIC THIAZOLO[2,3-B]-1,3,4-THIADIAZOLES AND N,N-BISHETEROARYLAMINES

被引：7
|
作者：
MOLINA, P
ARQUES, A
ALIAS, A
机构：
[1] Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, E-30071 Murcia, Campus de Espinardo
来源：
TETRAHEDRON | 1992年 / 48卷 / 07期
关键词：
IMINOPHOSPHORANE; AZA WITTIG-TYPE REACTION; MESOIONIC COMPOUNDS; N; N'-BISHETEROARYLGUANIDINES; N-BISHETEROARYLAMINES;
D O I：
10.1016/S0040-4020(01)90791-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aza Wittig-type reaction of iminophosphorane 1 derived from 3-amino-4-phenylthiazole-2(3H)-thione with several types of iso(thio)cyanates has been studied. The reaction of 1 with aromatic iso(thio)cyanates leads to thiazolo[2,3-b]-1,3,4-thiadiazoles 2 which display mesoionic character, whereas that with aliphatic isothiocyanates affords the betaines 3. N,N'-Bisheteroarylguanidines 5 are obtained from the reaction of 1 with aliphatic isocyanates; further treatment of compounds 5 with tetrafluoroboric acid leads to N,N'-bisheteroarylamines 8. The reaction of 1 with acyl chlorides affords thiazolo[2,3-b]-1,3,4-thiadiazolium salts 12.
引用
收藏
页码：1285 / 1298
页数：14
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