Synthesis of new heterocyclic system: 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione

Anton V. Dolzhenko, Anna V. Dolzhenko, Wai Keung Chui

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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.

Original languageEnglish
Pages (from-to)2049-2054
Number of pages6
JournalHeterocycles
Volume71
Issue number9
DOIs
Publication statusPublished - 1 Sep 2007
Externally publishedYes

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