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Synthesis 2004(9): 1359-1362  
DOI: 10.1055/s-2004-822397
PAPER
© Georg Thieme Verlag Stuttgart · New York

Facile One-Pot Synthesis of Di- and Tri-Substituted Furans From Acyl Isocyanates Using Trimethylsilyldiazomethane

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

Publication History

Received 2 May 2004
Publication Date:
08 June 2004 (online)

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Abstract

The Diels-Alder reaction of 2-substituted 4-(trimethyl­silyloxy)oxazoles, which were prepared in situ from trimethylsilyldiazomethane and acyl isocyanates, with dimethyl acetylenedicarboxylate or ethyl propiolate gave furan-3,4-dicarboxylic or furan-3-carboxylic esters in good yields.

Key words

acyl isocyanates - Diels-Alder reaction - furans - oxazoles - trimethylsilyldiazomethane

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