Synthesis of 3-arylazo-6-oxopyridazin-5-carbonitriles: A versatile precursor for condensed arylazopyridazin-6-ones

被引：6

作者：

Al-Mousawi, Saleh M. ^{[1
]}

El-Apasery, Morsy A. ^{[1
]}

Al-Kandery, Najat ^{[1
]}

Elnagdi, Mohamed H. ^{[1
]}

机构：

[1] Kuwait Univ, Fac Sci, Dept Chem, Kuwait 13060, Kuwait

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 02期

关键词：

D O I：

10.1002/jhet.5570450210

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-[2-Phenyl-1-diazenyl]-1-[2-phenylhydrazono] acetone or 1-[-2-(4-methylphenyl)-1-diazenyl]-1-[-2-(4-methylphenyl)hydrazono] -butan-2-one were produced via coupling the (E) 2-oxopropanal-1-phenyl-hydrazone or (E) 2-oxobutanal-1-(4-methylphenyl)hydrazone with aromatic diazonium salts. These formazanes condensed readily with ethyl cyanoacetate to yield 5-methyl-3-oxo-2-phenyl-6-phenlazo-2,3-dihydropyridazine-4-carbonitrile compound (9a), 5-ethyl-3-oxo-2-p-tolyl-6-p-tolylazo-2,3-dihydropyridazine-4-carbonitrile and/or 5-ethyl-3-oxo-2,6-di-p-tolyl-2,3-dihydropyridazine-4-carbonitrile that reacted with sulphur in presence of piperidine to yield the aminothienopyridazinones. The latter reacted with electron poor olefins and acetylenes to yield aminophthalazines. Compound (9a) reacted also with benzylidenemalononitrile to yield the arylazophthalazinone.

引用

页码：359 / 364

页数：6

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