Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione
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Open access
Authors
Dolzhenko, Anton
Dolzhenko, A.
Chui, W.
Date
2007Type
Journal Article
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Dolzhenko, Anton V. and Dolzhenko, Anna V. and Chui, Wai-Keung. 2007. Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione. Heterocycles. 71 (9): pp. 2049-2054.
Source Title
Heterocycles
ISSN
School
School of Pharmacy
Collection
Abstract
A synthesis of hitherto unknown heterocyclic system 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (5) is presented. The cyclocondensation of 2,6-diaminopyridine (1) with maleic anhydride yielded (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acid (2), which was converted to methyl (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl) acetate hydrochloride (3). The ester (3) upon treatment with sodium carbonate solution underwent intramolecular cyclization to 2a,3-dihydro-1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (4), which was oxidized in alkaline condition to provide 5.