TY - JOUR
T1 - Synthesis of Novel Dihydropyrimidines and Tetrahydropyrimidines
AU - Cho, Hidetsura
AU - Shima, Keiyuu
AU - Hayashimatsu, Mariko
AU - Ohnaka, Yoshiko
AU - Mizuno, Akira
AU - Takeuchi, Yumi
PY - 1985/11
Y1 - 1985/11
N2 - Condensation of alkyl 2-acetyl-3-aryl-2-propenoate with acetamidine, benzamidine, guanidine, or 1,1-dimethylguanidine followed by dehydration of the resulting compound 2 with p-TsOH or Al2O3 gave 1,4(3,4)-dihydropyrimidine 3. Regioselective alkoxycarbonylation, acylation, and alkylation of compound 3 with alkyl chloroformate, acyl halide, or alkyl halide in the presence of NaH afforded the series of novel N-substituted 3,4-dihydropyrimidines 4, 5, and 6 in good yield. Stereoselective NaBH4 reduction of the 3,4-dihydropyrimidine hydrochloride 4 provided a single stereoisomer of 1,2,3,4-tetrahydropyrimidine 7 whose stereochemistry was assigned as cis by X-ray crystallographic analysis. Conversely, the same reduction of the HCl salts of 3 or 6 gave a cis-trans mixture of tetrahydropyrimidines 8.
AB - Condensation of alkyl 2-acetyl-3-aryl-2-propenoate with acetamidine, benzamidine, guanidine, or 1,1-dimethylguanidine followed by dehydration of the resulting compound 2 with p-TsOH or Al2O3 gave 1,4(3,4)-dihydropyrimidine 3. Regioselective alkoxycarbonylation, acylation, and alkylation of compound 3 with alkyl chloroformate, acyl halide, or alkyl halide in the presence of NaH afforded the series of novel N-substituted 3,4-dihydropyrimidines 4, 5, and 6 in good yield. Stereoselective NaBH4 reduction of the 3,4-dihydropyrimidine hydrochloride 4 provided a single stereoisomer of 1,2,3,4-tetrahydropyrimidine 7 whose stereochemistry was assigned as cis by X-ray crystallographic analysis. Conversely, the same reduction of the HCl salts of 3 or 6 gave a cis-trans mixture of tetrahydropyrimidines 8.
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U2 - 10.1021/jo00222a009
DO - 10.1021/jo00222a009
M3 - Article
AN - SCOPUS:0000940050
VL - 50
SP - 4227
EP - 4230
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -