The Synthesis of 2-Cyano-cyanothioformanilides from 2-(4-Chloro-5H-1,2,3-dithiazol-5-ylideneamino)benzonitriles Using DBU

被引：24
|
作者：
Michaelidou, Sophia S. [1 ]
Koutentis, Panayiotis A. [1 ]
机构：
[1] Univ Cyprus, Dept Chem, CY-1678 Nicosia, Cyprus
来源：
SYNTHESIS-STUTTGART | 2009年 / 24期
关键词：
Appel salt; DBU; Cyanothioformanilide; isothiocyanate; RING-CLOSURE REACTIONS; ONE-STEP SYNTHESIS; NUCLEOPHILIC BEHAVIOR; CYCLIZATION REACTIONS; COMPLEX-FORMATION; FACILE SYNTHESIS; CYANOTHIOFORMAMIDES; CHEMISTRY; 3,1-BENZOTHIAZIN-4-ONES; 1,3,5-TRINITROBENZENE;
D O I：
10.1055/s-0029-1217059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)benzonitriles were prepared from the reaction of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) and the corresponding anthranilonitriles. Reaction of the 1,2,3-dithiazolimines with DBU (3 equiv) at -5 degrees C gave the corresponding 2-cyano-cyanothioformanilides in near quantitative yields. Treatment of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino) benzonitrile with DBU (4 equiv) at -5 to + 20 degrees C gave 2-isothiocyanatobenzonitrile in 96% yield. The latter compound was also formed directly from 2-cyano-cyanothioformanilide on treatment with DBU (1 equiv) in 95% yield. A tentative mechanism for the DBU-mediated dithiazole to cyanothioformanilide transformation is proposed and all compounds were fully characterized.
引用
收藏
页码：4167 / 4174
页数：8
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