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Synthesis 2011(6): 887-894  
DOI: 10.1055/s-0030-1258439
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Expeditious Synthesis of 2,3,6-Trisubstituted 2H-1,3-Oxazin-4(3H)-ones via the Tertiary Amine-Induced Reaction of 2-Diazo-3-oxoalkanals and Imines Under Mild Conditions

Hengzhen Qi, Jiantao Zhang, Jiaxi Xu*
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
Fax: +86(10)64435565; e-Mail: jxxu@mail.buct.edu.cn;
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Publication History

Received 13 January 2011
Publication Date:
11 February 2011 (online)

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Abstract

A series of 2,3,6-trisubstituted 2H-1,3-oxazin-4(3H)-one derivatives were conveniently synthesized in satisfactory to good yields by the reaction of imines with 2-diazo-3-oxoalkanals in the presence of a catalytic amount of a tertiary amine during several seconds under mild condition. Different bases and α-diazo-β-dicarbonyl compounds were also evaluated and a reaction mechanism is proposed. Compared with the corresponding thermal- and photo-induced­ reactions, the current method is a metal-free, mild, highly regioselective, and more efficient approach for the synthesis of 2H-1,3-oxazin-4(3H)-one derivatives.

Key words

acylketene - amine-induced reaction - cycloaddition - 2-diazo-3-oxoalkanal - Diels-Alder reaction - imine - oxazinone