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Synthesis 2007(2): 263-270
DOI: 10.1055/s-2006-958941
DOI: 10.1055/s-2006-958941
PAPER
© Georg Thieme Verlag Stuttgart · New York
Novel and Efficient Synthesis of 2-Aminooxazoles from Pyrimidin-2(1H)-one
Weitere Informationen
Received
21 August 2006
Publikationsdatum:
14. Dezember 2006 (online)
Publikationsverlauf
Publikationsdatum:
14. Dezember 2006 (online)
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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