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
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.