HMPA mediated one pot synthesis of 1-alkyl/aryl-4-dimethylamino[1,2,4]triazolo[4,3-a]quinoxalines

Citation
Vsh. Krishnan et al., HMPA mediated one pot synthesis of 1-alkyl/aryl-4-dimethylamino[1,2,4]triazolo[4,3-a]quinoxalines, I J CHEM B, 39(5), 2000, pp. 329-333
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
39
Issue
5
Year of publication
2000
Pages
329 - 333
Database
ISI
SICI code
0376-4699(200005)39:5<329:HMOPSO>2.0.ZU;2-7
Abstract
o-Phenylenediamine 1 is condensed with oxalic acid using Phillips' procedur e to obtain quinoxaline-2, 3-dione 2. The latter on treatment with hydrazin e hydrate gives the known 2-hydrazinoquinoxalin-3-one 3. Reaction of 3 with various acid chlorides (which were obtained from the corresponding carboxy lic acids by reaction with thionyl chloride in the presence of catalytic am ount of dimethyl formamide) in HMPA medium at 220 degreesC: in one pot reac tion yield the corresponding 1-substituted-4-dimethylamino[1, 2, 4]triazolo [4, 3-a]quinoxalines 4. This reaction has been shown to proceed through the intermediacy of 2-(N-acyl/aryl hydrazinoquinoxalin 3-one 5 and 1-substitut ed-4-oxo-[1, 2, 4] triazolo[4, 3-a]quinoxalines 6. An interesting observati on here has been that 5 can be cyclised to 6 at a considerably lower temper ature of 100 degrees than the requisite 220 degreesC using catalytic amount of HCl.