Volume 32, Issue 18
Heterocyclic Compounds
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ChemInform Abstract: Formation of 1,2-Oxazine Derivatives: A Novel Type of Reaction Between 2-Aminooxazoles and Maleic Acid Imide.

G. Ya. Kondrat'eva

G. Ya. Kondrat'eva

Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia

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M. A. Aitzhanova

M. A. Aitzhanova

Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia

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V. S. Bogdanov

V. S. Bogdanov

Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia

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G. A. Stashina

G. A. Stashina

Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia

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I. P. Sedishev

I. P. Sedishev

Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia

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First published: 27 May 2010

Abstract

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ChemInform Abstract

Reaction of N,N-disubstituted 2-aminooxazoles with maleimide (II) results in the formation of alkylidenesuccinimides (III) or pyrrolooxazines (V) depending on the substitution pattern of starting oxazoles. The formation of the fused heterocycles (V) is explained by an unprecedented C5—O bond cleavage of oxazoles (IV) followed by ring closure of the intramolecular diene synthesis type.

chemical structure image

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