Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-x]-azin-4-ones. A facile access to 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyridin-4-ones and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones

Citation
S. Recnik et al., Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-x]-azin-4-ones. A facile access to 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyridin-4-ones and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones, J HETERO CH, 37(4), 2000, pp. 783-790
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
4
Year of publication
2000
Pages
783 - 790
Database
ISI
SICI code
0022-152X(200007/08)37:4<783:CHO3>2.0.ZU;2-F
Abstract
By catalytic hydrogenation of 3-(benzyloxycarbonyl)amino-4H-pyrido[1,2-a]py ridin-4-ones 28 and 29, and azino[1,2-x]pyrimidin-4-ones 32-35, 41, and 42, partial saturation of the heterocyclic systems and removal of the benzylox ycarbonyl moiety was observed to give 3-amino-6,7,8,9-tetrahydro-4H-pyrido[ 1,2 a]pyridin-4-ones 30 and 31, and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2 -x]pyrimidin-4-ones 36-39, 43, and 44 in high yields. The methods represent a simple two step synthesis, starting from heterocyclic alpha-amino compou nds and methyl (Z)-2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate fol lowed by catalytic hydrogenation.