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Synthesis 2007(1): 97-107  
DOI: 10.1055/s-2006-958930
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Procedure for the Synthesis of 3-Substituted 5,6-Dihydro-4H-1,2-oxazines from Nitroethane

Alexey Yu. Sukhorukov, Michael S. Klenov, Pavel E. Ivashkin, Alexey V. Lesiv*, Yulya A. Khomutova, Sema L. Ioffe*
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(095)1355328; e-Mail: iof@ioc.ac.ru;
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Publication History

Received 16 June 2006
Publication Date:
12 December 2006 (online)

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Abstract

A novel and efficient four-step procedure for the synthesis of C-3-functionalised 5,6-dihydro-4H-1,2-oxazines from nitroethane is described. It includes preparation of 3-methyl-substituted six-membered cyclic nitronates, 3-(bromomethyl)-substituted 5,6-dihydro-4H-1,2-oxazines as intermediates, and nucleophilic substitution of bromine. Total yields of the target C-3-functionalised oxazines are 15-30% from nitroethane.

Key words

nitro compounds - heterocycles - 1,2-oxazines - silylation - unnatural amino acids

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