Synthesis of novel 1,4-, 3,4-, and 4,5-dihydropyrimidines: First successful POCl3 chlorination and regioselective alkoxycarbonylation

Hidetsura Cho; Yoshiko Ohnaka; Mariko Hayashimatsu; Masaru Ueda; Keiyuu Shima

doi:10.1016/S0040-4039(00)87813-2

Synthesis of novel 1,4-, 3,4-, and 4,5-dihydropyrimidines: First successful POCl₃ chlorination and regioselective alkoxycarbonylation

Hidetsura Cho, Yoshiko Ohnaka, Mariko Hayashimatsu, Masaru Ueda, Keiyuu Shima

PHA - Molecular Pharmaceutical Science

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

11 Citations (Scopus)

Abstract

Chlorination of 5,6-dihydropyrimidine-4-(3H)-one derivatives (1) with POCl₃ gave 1,4(3,4)-dihydropyrimidines (3), whose alkoxycarbonylation (ClCOOREt₃N or NaH) afforded regioselectively novel compounds (4). A new Pummerer type rearrangement of compound (1, XpS(O)CH₃) with POCl₃, gave compound (5h).

Original language	English
Pages (from-to)	6377-6380
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	52
DOIs	https://doi.org/10.1016/S0040-4039(00)87813-2
Publication status	Published - 1986

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{2771a1e45d6d468ab67c71f8f07b6974,

title = "Synthesis of novel 1,4-, 3,4-, and 4,5-dihydropyrimidines: First successful POCl3 chlorination and regioselective alkoxycarbonylation",

abstract = "Chlorination of 5,6-dihydropyrimidine-4-(3H)-one derivatives (1) with POCl3 gave 1,4(3,4)-dihydropyrimidines (3), whose alkoxycarbonylation (ClCOOREt3N or NaH) afforded regioselectively novel compounds (4). A new Pummerer type rearrangement of compound (1, XpS(O)CH3) with POCl3, gave compound (5h).",

author = "Hidetsura Cho and Yoshiko Ohnaka and Mariko Hayashimatsu and Masaru Ueda and Keiyuu Shima",

year = "1986",

doi = "10.1016/S0040-4039(00)87813-2",

language = "English",

volume = "27",

pages = "6377--6380",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "52",

}

TY - JOUR

T1 - Synthesis of novel 1,4-, 3,4-, and 4,5-dihydropyrimidines

T2 - First successful POCl3 chlorination and regioselective alkoxycarbonylation

AU - Cho, Hidetsura

AU - Ohnaka, Yoshiko

AU - Hayashimatsu, Mariko

AU - Ueda, Masaru

AU - Shima, Keiyuu

PY - 1986

Y1 - 1986

N2 - Chlorination of 5,6-dihydropyrimidine-4-(3H)-one derivatives (1) with POCl3 gave 1,4(3,4)-dihydropyrimidines (3), whose alkoxycarbonylation (ClCOOREt3N or NaH) afforded regioselectively novel compounds (4). A new Pummerer type rearrangement of compound (1, XpS(O)CH3) with POCl3, gave compound (5h).

AB - Chlorination of 5,6-dihydropyrimidine-4-(3H)-one derivatives (1) with POCl3 gave 1,4(3,4)-dihydropyrimidines (3), whose alkoxycarbonylation (ClCOOREt3N or NaH) afforded regioselectively novel compounds (4). A new Pummerer type rearrangement of compound (1, XpS(O)CH3) with POCl3, gave compound (5h).

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U2 - 10.1016/S0040-4039(00)87813-2

DO - 10.1016/S0040-4039(00)87813-2

M3 - Article

AN - SCOPUS:0000355354

VL - 27

SP - 6377

EP - 6380

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -