1,3-Dipolar Cycloaddition of Nitrile Imines with Cyclic α-β-Unsaturated Ketones: A Regiochemical Route to Ring-Fused Pyrazoles

被引：28

作者：

Chandanshive, Jay Zumbar ^{[1
]}

Bonini, Bianca Flavia ^{[1
]}

Tiznado, William ^{[2
]}

Escobar, Carlos A. ^{[2
]}

Caballero, Julio ^{[3
]}

Femoni, Cristina ^{[1
]}

Fochi, Mariafrancesca ^{[1
]}

Franchini, Mauro Comes ^{[1
]}

机构：

[1] Univ Bologna UNIBO, Dept Organ Chem, I-40136 Bologna, Italy

[2] Univ Andres Bello, Dept Ciencias Quim, Fac Ecol & Recursos Nat, Santiago, Chile

[3] Univ Talca, Ctr Bioinformt & Simulac Mol, Fac Ingn Bioinformat, Talca, Chile

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 25期

关键词：

Cycloaddition; Nitrile imines; Ketones; Fused-ring systems; Computational chemistry; CARBONATE PROMOTED REACTION; BIOLOGICAL EVALUATION; QUANTITATIVE CHARACTERIZATION; DIAZOCARBONYL COMPOUNDS; HYDRAZONYL CHLORIDES; AZOMETHINE YLIDES; REGIOSELECTIVITY; INHIBITORS; ELECTROPHILICITY; DERIVATIVES;

D O I：

10.1002/ejoc.201100558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with cyclic alpha,beta-unsaturated ketones of various sizes have been studied. After cycloaddition, oxidative aromatization gives the ring-fused pyrazoles. Computational studies and the use of topological analyses of the Fukui functions allows a theoretical description of the local reactivity that is in agreement with the experimentally observed regiochemistry.

引用

页码：4806 / 4813

页数：8

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