Transformations of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one under various conditions of cyclopropyldiazonium generation

被引：2

作者：

Okonnishnikova, G. P. ^{[1
]}

Kostyuchenko, I. V. ^{[1
]}

Shulishov, E. V. ^{[1
]}

Tomilov, Yu. V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2006年 / 55卷 / 12期

关键词：

cyclopropyldiazonium; cyclopropylhydrazone; N-cyclopropylnitrone; spiro[isoxazolidine-3,4 '-pyrazoline; azo coupling; nitrosation; 1,3-dipolar addition;

D O I：

10.1007/s11172-006-0577-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclopropyldiazonium generated by basic decomposition of N-cyclopropyl-N-nitrosourea easily entered into an azo coupling reaction with 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2) to give the corresponding cyclopropylhydrazone in up to 90% yield. Competitive processes occurring under the conditions of cyclopropyldiazonium generation by nitrosation of cyclopropylamine with butyl nitrite mainly include nitrosation of the starting pyrazolone 2. Subsequent transformations of the resulting heterocyclic 3-methyl-1-phenyl-1H-pyrazole-4,5-dione 4-oxime yield 4-[cyclopropyl(oxido)imino]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one.

引用

页码：2233 / 2237

页数：5

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