Synthesis and structure of benzimidazo[1,2-c][1,2,3]thiadiazoles: first examples of a novel ring system

被引:14
作者
Tumkevicius, S [1 ]
Labanauskas, L [1 ]
Bucinskaite, V [1 ]
Brukstus, A [1 ]
Urbelis, G [1 ]
机构
[1] Vilnius State Univ, Fac Chem, Dept Organ Chem, LT-2006 Vilnius, Lithuania
关键词
D O I
10.1016/S0040-4039(03)01672-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(1-Amino-1H-benzimidazol-2-yl)methanol 1 with thionyl chloride at reflux afforded 3-chlorobenziinidazo[1,2-c][1,2,3]thiadiazole 4, which reacted with various nucleophiles to give different products depending on the nature of the solvent. The structures of 4 and di(benzimidazo[1,2-c][1,2,3]thiadiazol-3-yl)sulfide 8 were confirmed by single-crystal X-ray analysis. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6635 / 6638
页数:4
相关论文
共 29 条
[1]   Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates [J].
Abramov, MA ;
Dehaen, W ;
D'hooge, B ;
Petrov, ML ;
Smeets, S ;
Toppet, S ;
Voets, M .
TETRAHEDRON, 2000, 56 (24) :3933-3940
[2]  
BOWLES SA, Patent No. 9315047
[3]   NOVEL 1,2,3-THIADIAZOLYL SULFINES FROM THE REACTION OF N-SUBSTITUTED HYDRAZONES WITH THIONYL CHLORIDE [J].
BRITTON, TC ;
LOBL, TJ ;
CHIDESTER, CG .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4773-4780
[4]  
Brukshtus A, 1996, KHIM GETEROTSIKL+, P427
[5]   A facile synthesis of benzo[4,5]imidazo[2,1-b]pyrimido[5,4-f][1,3,4]thiadiazepines [J].
Brukstus, A ;
Melamedaite, D ;
Tumkevicius, S .
SYNTHETIC COMMUNICATIONS, 2000, 30 (20) :3719-3730
[6]  
CLARK T, 1999, VAMP VERSION 7 5A
[7]  
ESSASSI EM, 1994, B SOC CHIM BELG, V103, P83
[8]   PREPARATION OF BETA-HYDROXYSULFIDES FROM 1,2,3-THIADIAZOLES - COMPARISON OF THE EFFECT OF PHENYLMAGNESIUM BROMIDE ON ALPHA-THIOKETONES AND ALPHA-SELENOKETONES [J].
GANJIAN, I .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (07) :2037-2039
[9]  
Garaliene V, 1998, ARZNEIMITTEL-FORSCH, V48, P1137
[10]   ON ACYLHYDRAZONES AND 1,2,3-THIADIAZOLES [J].
HURD, CD ;
MORI, RI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (20) :5359-5364