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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

✍ Scribed by Simon Rečnik; Renata Toplak; Jurij Svete; Lucija Pizzioli; Branko Stanovnik

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
615 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

By catalytic hydrogenation of 3‐(benzyloxycarbonyl)amino‐4__H__‐pyrido[1,2‐a]pyridin‐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 benzyloxycarbonyl moiety was observed to give 3‐amino‐6,7,8,9‐tetrahydro‐4__H__‐pyrido[1,2 a]pyridin‐4‐ones 30 and 31, and 3‐amino‐6,7,8,9‐tetrahydro‐4__H__‐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 α‐amino compounds and methyl (Z)‐2‐(benzyloxycarbonyl)amino‐3‐dimethylaminopropenoate followed by catalytic hydrogenation.

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ChemInform Abstract: Catalytic Hydrogena
ChemInform Abstract: 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.
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