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Paper | Regular issue | Vol 78, No. 10, 2009, pp.2477-2488
Published online, 2nd July, 2009
DOI: 10.3987/COM-09-11746
Synthesis of Halogenated 4H-Pyrido[1,2-a]pyrimidin-4-ones

Annamária Molnár, Ferenc Faigl, Benjamin Podányi, Zoltán Finta, László Balázs, and István Hermecz*

*R & D Directorate Preclinical Development, CHINOIN Pharmaceutical and Chemical Works Ltd., P. O. Box 110, H-1325 Budapest, Hungary


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]pyrimidin-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 “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 1H NMR and 13C NMR examinations.