One-Pot Highly Regioselective Synthesis of α-Ketoamide N-Arylpyrazoles from Secondary β-Enamino Diketones

被引：17

作者：

Poletto, Julia ^{[1
]}

Ribeiro, Gessica M. ^{[1
]}

da Silva, Michael J., V ^{[1
]}

Jacomini, Andrey P. ^{[1
]}

Basso, Ernani A. ^{[1
]}

Back, Davi F. ^{[2
]}

Moura, Sidnei ^{[3
]}

Rosa, Fernanda A. ^{[1
]}

机构：

[1] Univ Estadual Maringa, Dept Quim, BR-87030900 Maringa, Parana, Brazil

[2] Univ Fed Santa Maria, Dept Quim, BR-97110970 Santa Maria, RS, Brazil

[3] UCS, Inst Biotecnol, BR-29507056 Caxias Do Sul, RS, Brazil

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 16期

关键词：

PYRAZOLE;

D O I：

10.1021/acs.orglett.9b02206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot method is described for the highly regioselective synthesis of alpha-ketoamide N-arylpyrazoles from secondary beta-enamino diketones. For this, the key intermediate, 4-acyl 3,5-dihydroxypyrrolone, was generated in situ and underwent bimolecular nucleophilic substitution at C-5 by arylhydrazine, with subsequent heterocyclization at the carbonyl carbon of the acyl group. This strategy allowed for regiochemical control of alpha-ketoamide N-arylpyrazoles from beta-enamino diketones and arylhydrazines.

引用

页码：6325 / 6328

页数：4

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