SYNTHESIS OF 6,7-DIHYDROPYRIDO[2,3-d]PYRIMIDIN-5(8H)-ONE DERIVATIVES BASED ON THE REACTION OF 1-(4-CHLOROPYRIMIDIN-5-YL)ALK-2-EN-1-ONE DERIVATIVES WITH PRIMARY AMINES

被引：6

作者：

Kobayashi, Kazuhiro ^{[1
]}

Ono, Ryoga ^{[1
]}

Ishitobi, Kouki ^{[1
]}

Chikazawa, Yuuki ^{[1
]}

Hiyoshi, Hidetaka ^{[2
]}

Umezu, Kazuto ^{[2
]}

机构：

[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Div Appl Chem, 4-101 Koyama Minami, Tottori 6808552, Japan

[2] Ihara Chem Ind Co Ltd, Dev Sect, Mkt & Dev Dept, Mkt Div,Taito Ku, 4-26 Ikenohata 1 Chome, Tokyo 1100008, Japan

来源：

HETEROCYCLES | 2016年 / 92卷 / 02期

关键词：

INHIBITORS; PYRIMIDINES; DESIGN;

D O I：

10.3987/COM-15-13373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient sequence for the synthesis of 6,7-dihydropyrido[2,3-d]pyrimidin-5(8H)-one derivatives has been developed. Thus, treatment of 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine with lithium diisopropylamide (LDA) generates 4-chloro-5-lithio-6-methoxy-2(methylsulfanyl)pyrimidine, which are allowed to react with alpha,beta-unsaturated aldehydes to give the corresponding 1-(4-chloropyrimidin-5-yl)alk-2-en-1-ol derivatives. Oxidation of these alkenols with activated manganese(IV) oxide provides 1-(4-chloropyrimidin-5-yl)alk-2-en-1-one derivatives, of which reaction with a variety of primary amines constitutes tetrahydropyridinone structure to give the desired products.

引用

页码：260 / 271

页数：12

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