Regioselective synthesis of fused pyrazolo[1,5-a]pyrimidines by reaction of 5-amino-1H-pyrazoles and β-dicarbonyl compounds containing five-membered rings

被引：34

作者：

Portilla, Jaime ^{[1
]}

Quiroga, Jairo ^{[2
]}

Nogueras, Manuel ^{[3
]}

Cobo, Justo ^{[3
]}

机构：

[1] Univ Los Andes, Dept Chem, Bioorgan Cpds Res Grp, Bogota, Colombia

[2] Univ Valle, Dept Chem, Heterocycl Cpds Res Grp, Cali 25360, Colombia

[3] Univ Jaen, Dept Inorgan & Organ Chem, Jaen 23071, Spain

来源：

TETRAHEDRON | 2012年 / 68卷 / 04期

关键词：

5-Amino-1H-pyrazoles; 2-Aacetylcyclopentanone; 2-Ethoxycarbonylcyclopentanone; 2-Acetylbutyrolactone; Pyrazolo[1,5-a]pyrimidine; SOLVENT; DERIVATIVES; ANTAGONISTS; FORMYLATION; POTENT; ROUTES;

D O I：

10.1016/j.tet.2011.12.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 3-substituted-5-amino-1H-pyrazoles with 2-acetylcyclopentanone or 2-ethoxycarbonylcyclopentanone lead to the regioselective formation of a new series of cyclopentapyrazolo[1,5-a]pyrimidines in good yields. When 2-acetylbutyrolactone was used, the reaction provided 6-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidinone and/or the intermediate (3Z)-3-{1-[(5-R-1H-pyrazol-3-yl) amino]ethylidene}-4,5-dihydrofuranone. This indicates that the cyclization proceeds with butyrolactone ring opening as the last step. Several aspects of this regioselective reaction, including mechanistic and structural studies, are considered. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：988 / 994

页数：7

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