Synthesis of Novel Dihydropyrimidines and Tetrahydropyrimidines

Hidetsura Cho, Keiyuu Shima, Mariko Hayashimatsu, Yoshiko Ohnaka, Akira Mizuno, Yumi Takeuchi

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4227-4230
Number of pages4
JournalJournal of Organic Chemistry
Volume50
Issue number22
DOIs
Publication statusPublished - 1985 Nov

ASJC Scopus subject areas

  • Organic Chemistry

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