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Note | Regular issue | Vol 71, No. 9, 2007, pp.2049-2054
Published online, 12th June, 2007
DOI: 10.3987/COM-07-11092
Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione

Anton V. Dolzhenko, Anna V. Dolzhenko, and Wai-Keung Chui*

*Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore


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.