2H-BENZIMIDAZOLES (ISOBENZIMIDAZOLES) .10. SYNTHESIS OF POLYSUBSTITUTED O-PHENYLENEDIAMINES AND THEIR CONVERSION INTO HETEROCYCLES, PARTICULARLY 2-SUBSTITUTED BENZIMIDAZOLES WITH KNOWN OR POTENTIAL ANTHELMINTIC ACTIVITY

被引：49

作者：

HAZELTON, JC ^{[1
]}

IDDON, B ^{[1
]}

SUSCHITZKY, H ^{[1
]}

WOOLLEY, LH ^{[1
]}

机构：

[1] UNIV SALFORD, SCI RES INST, DIV CHEM SCI, SALFORD M5 4WT, LANCS, ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 39期

关键词：

D O I：

10.1016/0040-4020(95)00642-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polysubstituted o-phenylenediamines were synthesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio- and 2-trifluoromethylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)benzimidazole and 11-(pridin-2-ylthio)dibenzo[a,c]phenazine were synthesised too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.

引用

页码：10771 / 10794

页数：24

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