SYNTHESIS OF HALOGENATED 4H-PYRIDO[1,2-a]PYRIMIDIN-4-ONES

被引：14

作者：

Molnar, Annamaria ^{[1
,2
]}

Faigl, Ferenc ^{[2
,3
]}

Podanyi, Benjamin ^{[1
]}

Finta, Zoltan ^{[1
]}

Balazs, Laszlo ^{[1
]}

Hermecz, Istvan ^{[1
,2
]}

机构：

[1] Chinoin Chem & Pharmaceut Works Ltd, H-1045 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary

[3] Hungarian Acad Sci, Res Grp Organ Chem Technol, H-1111 Budapest, Hungary

来源：

HETEROCYCLES | 2009年 / 78卷 / 10期

关键词：

Thermal Cyclization; 4H-Pyrido[1,2-a]pyrimidin-4-one; 1,4-Dihydro-1,8-naphthyridin-4-one; 4+2] Cycloaddition; Tetrahydropyridine-2,4-dione; NITROGEN-BRIDGEHEAD COMPOUNDS; EFFLUX PUMP INHIBITORS; RING TRANSFORMATION; MELDRUMS ACID; PSEUDOMONAS-AERUGINOSA; RECEPTOR; ANALOGS; DERIVATIVES; ANTAGONISTS; KETANSERIN;

D O I：

10.3987/COM-09-11746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halogenated 4H-pyrido[1,2-a]pyrimidin-4-one were synthesized by thermal cyclization and decarboxylation of isopropylidene (2-pyridylamino)methylenemalonates, prepared from 2-aminopyridines and isopropylidene methoxymethylenemalonate formed in situ. Instead of 4H-pyrido[1,2-a]pyrmidin-4-ones, the 6-chloro and 6-bromo derivatives afforded mixtures of 7-halo-1,4-dihydro-1,8-naphthyridin-4-ones and 1-(6-halo-2-pyridyl)-3[(6-halo-2-pyridylamino)methylene]-1,2,3,4-tetrahydropyridine-2,4-diones. The latters formed from N-(2-pyridyl)iminoketenes, the common intermediates of 4H-pyrido[1,2-a]pyrimidin-4-one and 1,8-naphthyridin-4-ones, via a a "head-to-tail" [4+2] cycloaddition. 3-Halo-4H-pyrido[1,2-a]pyrimidin-4-ones were obtained from 4H-pyrido[1,2-a]pyrimidin-4-one with N-halosuccinimides. The structures of the new compounds were characterized by means of H-1 NMR and C-13 NMR examinations.

引用

页码：2477 / 2488

页数：12

共 50 条

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