Facile, One-Pot Synthesis of Bicyclic 2-Pyridones from Acyl Isocyanates, N-Phenylmaleimide and Trimethylsilyldiazomethane

Yoshiyuki Hari; Tomoe Iguchi; Toyohiko Aoyama

doi:10.1055/s-2005-870002

PAPER

Facile, One-Pot Synthesis of Bicyclic 2-Pyridones from Acyl Isocyanates, N-Phenylmaleimide and Trimethylsilyldiazomethane

Yoshiyuki Hari, Tomoe Iguchi, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho, Nagoya 467-8603, Japan
Fax: +81(52)8363439; e-Mail: aoyama@phar.nagoya-cu.ac.jp;

Abstract

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Abstract

The hetero-Diels-Alder reaction of 2-substituted 4-trimethylsiloxyoxazoles, prepared in situ from trimethylsilyldiazomethane and acyl isocyanates, with N-phenylmaleimide followed by treatment with a catalytic amount of 10-camphorsulfonic acid efficiently gave bicyclic 2-pyridones in a one-pot process.

Key words

acyl isocyanates - Diels-Alder reaction - 2-pyridones - oxazoles - trimethylsilyldiazomethane

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