TY - JOUR
T1 - Synthesis and Rearrangement of 2-Oxo-3-phenylisoxazolo[2,3-α]pyrimidines
AU - Zvilichovsky, Gury
AU - Gurvich, Vadim
AU - Segev, Shlomo
PY - 1995/8/1
Y1 - 1995/8/1
N2 - 2-Oxo-3-phenylisoxazolo[2,3-α]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl methyl ethers. The structures of these 2-oxoisoxazolo[2,3-α]pyrimidines and the mechanism of their rearrangement is discussed.
AB - 2-Oxo-3-phenylisoxazolo[2,3-α]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl methyl ethers. The structures of these 2-oxoisoxazolo[2,3-α]pyrimidines and the mechanism of their rearrangement is discussed.
UR - http://www.scopus.com/inward/record.url?scp=0029120156&partnerID=8YFLogxK
U2 - 10.1021/jo00121a049
DO - 10.1021/jo00121a049
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AN - SCOPUS:0029120156
SN - 0022-3263
VL - 60
SP - 5250
EP - 5254
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -