Synthesis of 3-substituted 3,4-dihydropyrimidines: N-Alkoxycarbonylation with trichloromethyl chloroformate and alcohols

Hidetsura Cho; Akira Mizuno; Keiyuu Shima; Masaru Ueda; Yumi Takeuchi; Mikiko Hamaguchi; Nobuaki Taniguchi

doi:10.3987/COM-87-4417

Synthesis of 3-substituted 3,4-dihydropyrimidines: N-Alkoxycarbonylation with trichloromethyl chloroformate and alcohols

Hidetsura Cho, Akira Mizuno, Keiyuu Shima, Masaru Ueda, Yumi Takeuchi, Mikiko Hamaguchi, Nobuaki Taniguchi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

N-Alkoxycarbonylation reactions of dihydropyrimidines with trichloromethyl chloroformate (phosgene dimer) and an alcohol were carried out in order to obtain the dihydropyrimidines with a complicated alkyl group or an alkyl group containing a nitrogen atom. Especially, the synthetically difficult problem of the unstable N-substituted dihydropyrimidines containing a nitrogen atom in an ester group was overcome by the method II: 0.5-1.2 mol equiv. of phosgene dimer, 1.0-6.0 equiv. of tertiary aminoalcohol, and 6 equiv. of Et₃N in THF at -23 °C-r.t.

Original language	English
Pages (from-to)	769-774
Number of pages	6
Journal	Heterocycles
Volume	27
Issue number	3
DOIs	https://doi.org/10.3987/COM-87-4417
Publication status	Published - 1988 Mar 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "N-Alkoxycarbonylation reactions of dihydropyrimidines with trichloromethyl chloroformate (phosgene dimer) and an alcohol were carried out in order to obtain the dihydropyrimidines with a complicated alkyl group or an alkyl group containing a nitrogen atom. Especially, the synthetically difficult problem of the unstable N-substituted dihydropyrimidines containing a nitrogen atom in an ester group was overcome by the method II: 0.5-1.2 mol equiv. of phosgene dimer, 1.0-6.0 equiv. of tertiary aminoalcohol, and 6 equiv. of Et3N in THF at -23 °C-r.t.",

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T1 - Synthesis of 3-substituted 3,4-dihydropyrimidines

T2 - N-Alkoxycarbonylation with trichloromethyl chloroformate and alcohols

AU - Cho, Hidetsura

AU - Mizuno, Akira

AU - Shima, Keiyuu

AU - Ueda, Masaru

AU - Takeuchi, Yumi

AU - Hamaguchi, Mikiko

AU - Taniguchi, Nobuaki

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AB - N-Alkoxycarbonylation reactions of dihydropyrimidines with trichloromethyl chloroformate (phosgene dimer) and an alcohol were carried out in order to obtain the dihydropyrimidines with a complicated alkyl group or an alkyl group containing a nitrogen atom. Especially, the synthetically difficult problem of the unstable N-substituted dihydropyrimidines containing a nitrogen atom in an ester group was overcome by the method II: 0.5-1.2 mol equiv. of phosgene dimer, 1.0-6.0 equiv. of tertiary aminoalcohol, and 6 equiv. of Et3N in THF at -23 °C-r.t.

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Synthesis of 3-substituted 3,4-dihydropyrimidines: N-Alkoxycarbonylation with trichloromethyl chloroformate and alcohols

Abstract

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