Synthesis of 4-unsubstituted dihydropyrimidines. Nucleophilic substitution at position-2 of dihydropyrimidines

被引：27

作者：

Cho, Hidetsura ^{[1
,2
]}

Nishimura, Yoshio ^{[2
,5
]}

Yasui, Yoshizumi ^{[3
]}

Kobayashi, Satoshi ^{[2
]}

Yoshida, Shin-ichiro ^{[1
,4
]}

Kwon, Eunsang ^{[1
,4
]}

Yamaguchi, Masahiko ^{[2
,3
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

[3] Tohoku Univ, WPI Adv Inst Mat Res, Sendai, Miyagi 9808578, Japan

[4] Tohoku Univ, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan

[5] Yasuda Womens Univ, Fac Pharm, Asaminami Ku, Hiroshima 7310153, Japan

来源：

TETRAHEDRON | 2011年 / 67卷 / 14期

关键词：

Dihydropyrimidine; Tautomerism; Individual tautomer; X-ray diffraction; Nucleophilic substitution; 2,3,5,8-Tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine; CALCIUM-CHANNEL BLOCKERS; ACID-ESTERS; POTENT MIMICS; TAUTOMERISM;

D O I：

10.1016/j.tet.2011.01.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of novel 4-unsubstituted dihydropyrimidines (DPs) was performed. Subsequently, a variety of 4-unsubstituted 1,4(3,4)-DPs with amino moieties at position-2 were obtained in excellent yields by activation of position-2 owing to regioselective alkoxycarbonylation at position-3 of the DP skeleton. 3-Oxo-2-phenyl-2,3,5,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine was obtained using phenylhydrazine instead of amines. Individual tautomers of 1,4(3,4)-DP were observed in the H-1 NMR spectra of one derivative depending on temperature and concentration. On the other hand, only 1,4-DP was found in the solid state by single-crystal X-ray crystallography. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2661 / 2669

页数：9

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