Straightforward and regiospecific synthesis of pyrazole-5-carboxylates from unsymmetrical enaminodiketones

被引：63

作者：

Rosa, Fernanda A. ^{[1
]}

Machado, Pablo ^{[1
]}

Vargas, Pamela S. ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

Zanatta, Nilo ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNLETT | 2008年 / 11期

关键词：

enones; cyclizations; regioselectivity; pyrazoles; heterocycles;

D O I：

10.1055/s-2008-1078482

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 4-substituted 1H-pyrazole-5-carboxylates was prepared from the cyclocondensation reaction Of Unsymmetrical enaminodiketones [RC(O)C(=CNMe(2))C(O)CO(2)Et, where R = Ph, 4-MeOC(6)H(4), 4-ClC(6)H(4), 4-FC(6)H(4), 4-O(2)NC(6)H(4), thien-2-yl, benzofur-2-yl, CCl(3) and CF(3)] with tert-butylhydrazine hydrochloride or carboxymethylhydrazine. The compounds were obtained regiospecifically and in good to excellent yields (73-94%). In addition, 5-carboxyethyl-1-(1, 1-dimethylethyl)-1H-pyrazole-4-carboxylic acid was synthesized from regiospecific conversion of ethyl 4-(2,2,2-trichloroacetyl)-1-(1, 1-dimethylethyl)-1H-pyrazole-5-carboxylate. The carbonyl substitution reaction was regiospecific for the trichloroacetyl group and did not affect the ester group.

引用

页码：1673 / 1678

页数：6

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