TITLE:
Some New Heterocycles from the Reaction of 4-Carboxaldehyde-2-Phenyl-2H-1,2,3-Triazole Malononitrile
AUTHORS:
Mohamed A. El Sekily, Sohayla H. Mancy, A. M. El-Ghanam, G. A. Leon
KEYWORDS:
Triazoles, Triazole Malononitrile, Pyrazole, Isoxazole
JOURNAL NAME:
Natural Science,
Vol.9 No.12,
December
15,
2017
ABSTRACT:
Reaction of 4-carboxaldehyde-2-phenyl-2H-1,2,3-triazole 1 with
malononitrile in presence of piperidine afforded the triazolomalonitrile 2
which on treatment with hydrazine hydrate, gave
3-amino-5-(2-phenyl-2H-1,2,3-triazol-4-yl)-4,5-dihydro-1-H-pyrazole-4-carbonitrile
3 and with hydroxylamine, gave
5-amino-3-(2-phenyl-2H-1,2,3-triazol-4-yl)-2,3-dihydroisoxazole-4-carbonitrile
4, and with thiourea,
gave2,4-diamino-6-(2-phenyl-2H-1,2,3-triazol-4-yl)-6H-1,3-thiazine-5-carbonitrile
5. Similarly, reaction of 2 with ethanol amine, gave
2-amino-4-(2-phenyl-2H-1,2,3-triazol-4-yl)nicotinonitrile 6, and with
thiosemicarbazide,gave
4-amino-2-hydrazinyl-6-(2-phnyl-2H-1,2,3-triazol-4-yl)-6H-1,3-thiazine-carbonitrile7.
Similary reaction of 2 with cyclopentanone gave,
2-amino-4-(2-phenyl-2H-1,2,3-triazol-4-yl)-4,5,6,7-tetrahydrocyclopenta
[6] pyran-3-carbonitrile 8. In addition, reaction of 1 with hydrazine hydrate,
gave the 4 hydrazone which on treatment with another mole of 1 gave 10 and with
3-carboxaldehyde-1-phenyl-4,5-pyrazolinedione 4 phenylhydrazone gave compound
11.