TY - JOUR
T1 - Synthesis of new heterocyclic system
T2 - 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione
AU - Dolzhenko, Anton V.
AU - Dolzhenko, Anna V.
AU - Chui, Wai Keung
N1 - Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2007/9/1
Y1 - 2007/9/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=35748929123&partnerID=8YFLogxK
U2 - 10.3987/com-07-11092
DO - 10.3987/com-07-11092
M3 - Article
AN - SCOPUS:35748929123
VL - 71
SP - 2049
EP - 2054
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 9
ER -