Unconventional Method for Synthesis of 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles,The Journal of Organic Chemistry

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Unconventional Method for Synthesis of 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-15 00:00:00 , DOI: 10.1021/acs.joc.7b02361
Michael J. V. da Silva ₁ , Julia Poletto ₁ , Andrey P. Jacomini ₁ , Karlos E. Pianoski ₁ , Davana S. Gonçalves ₁ , Gessica M. Ribeiro ₁ , Samara M. de S. Melo ₁ , Davi F. Back ₂ , Sidnei Moura ₃ , Fernanda A. Rosa ₁

Affiliation

An alternative highly regioselective synthetic method for the preparation of 3,5-disubstituted 4-formyl-N-arylpyrazoles in a one-pot procedure is reported. The methodology developed was based on the regiochemical control of the cyclocondensation reaction of β-enamino diketones with arylhydrazines. Structural modifications in the β-enamino diketone system allied to the Lewis acid carbonyl activator BF₃ were strategically employed for this control. Also a one-pot method for the preparation of 3,5-disubstituted 4-hydroxymethyl-N-arylpyrazole derivatives from the β-enamino diketone and arylhydrazine substrates is described.

中文翻译：

非传统方法合成3-羧乙基-4-甲酰基（羟基）-5-芳基-N-芳基吡唑

报道了一种通过一锅法制备3,5-二取代的4-甲酰基-N-芳基吡唑类化合物的另一种高度区域选择性的合成方法。所开发的方法基于对β-烯氨基二酮与芳基肼的环缩合反应的区域化学控制。与路易斯酸羰基活化剂BF ₃相关联的β-烯氨基二酮系统的结构修饰被策略性地用于该控制。还描述了一种由一锅法从β-烯氨基二酮和芳基肼底物制备3，5-二取代的4-羟甲基-N-芳基吡唑衍生物的方法。

更新日期：2017-11-16

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