Novel and Efficient Synthesis of 2-Aminooxazoles from Pyrimidin-2(1H)-one

Vadim L. Alifanov; Eugene V. Babaev

doi:10.1055/s-2006-958941

PAPER

Novel and Efficient Synthesis of 2-Aminooxazoles from Pyrimidin-2(1H)-one

Vadim L. Alifanov, Eugene V. Babaev*
Chemistry Department, Moscow State University, Moscow 119992, Russian Federation
Fax: +7(495)9393020; e-Mail: babaev@org.chem.msu.su;

Abstract

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Abstract

Stepwise conversion of pyrimidin-2(1H)-one to 2-amino-5-aryloxazoles via oxazolo[3,2-a]pyrimidinium salts is reported. The sequence involves, (i) regioselective N-alkylation of pyrimidone by phenacyl bromides, (ii) cyclization of obtained 1-(2-aryl-2-oxoethyl)pyrimidin-2(1H)-ones into oxazolo[3,2-a]pyrimidinium salts under the action of fuming sulfuric (or triflic) acid, and (iii) reaction of the obtained salts with hydrazine leading to 2-amino-5-aryloxazoles.

Key words

fused ring systems - ring closure - ring opening - oxazoles - protecting groups

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References

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