Efficient regioselective synthesis of 6-amino-5-benzoyl-1-substituted 2(1H)-pyridinones

被引：53

作者：

Schirok, H ^{[1
]}

Alonso-Alija, C ^{[1
]}

Benet-Buchholz, J ^{[1
]}

Göller, AH ^{[1
]}

Grosser, R ^{[1
]}

Michels, M ^{[1
]}

Paulsen, H ^{[1
]}

机构：

[1] Bayer HealthCare, Pharma Res, D-42096 Wuppertal, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 23期

关键词：

D O I：

10.1021/jo0515428

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective and efficient approach toward 6-amino-5-benzoyl-1-substituted 2(1H)-pyridinones by reaction of acyclic ketene aminals with propiolic acid ester was developed. The effect of the solvent and temperature on the regioselectivity of the reaction and the compatibility of the target compounds to functional group manipulations was examined. Substrates with an ortho substituent build atropisomers due to the restricted rotation around the C-N bond. The enantiomers were separated, and the barrier of rotation was determined experimentally. Quantum chemical calculations allowed a ranking of the barrier heights, and a new mechanism of rotation by deformation of the central pyridinone moiety is proposed.

引用

页码：9463 / 9469

页数：7

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