GSC  Vol.2 No.2 , May 2012
Aspects on the Mechanism of the 1-Phenyl-1H-pyrazolo[3,4-b]quinoxaline Formation
Abstract: Condensation of D-glucose, o-phenylenediamine and N,N-benzylphenylhydrazine hydrochloride (NNBPHH) in a one-pot reaction, or condensation of 2-(D-arabino-tetritol-1-yl) quinoxaline and NNBPHH, gave 3-(D-erythro-glycerol-1- yl)-1-phenyl-1H-pyrazolo[3,4-b]quinoxaline. The structure of the latter was determined by 1H NMR spectroscopy and by synthesis using phenylhydrazine hydrochloride instead of NNBPHH. Condensation of D-glucose and 4,5-dichloro-o-phenylenediamine gave 6,7-dichloro-2-(D-arabino-tetritol-1-yl)quinoxaline, which upon condensation with NNBPHH gave the corresponding 6,7-dichloro-3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo[3,4-b]quinoxaline. The structure and mechanism of formation of these compounds are discussed.
Cite this paper: M. A. Mostafa, S. L. Aboulela, M. A. E. Sallam, F. F. Louis and T. Anthonsen, "Aspects on the Mechanism of the 1-Phenyl-1H-pyrazolo[3,4-b]quinoxaline Formation," Green and Sustainable Chemistry, Vol. 2 No. 2, 2012, pp. 71-75. doi: 10.4236/gsc.2012.22012.

[1]   M. A. Mostafa, “Aspects on Pyrazolo[3,4-b]quinoxaline Formation,” Bulletin of the Faculty of Science, Alexandria University, Vol. 29, No. 2-3, 1989, pp. 35-44.

[2]   A. S. Shawali, M. M. Zayed and T. A. Farghaly, “Synthesis and Biological Activity of New 1H-Pyrazolo[3,4-b] quinoxalines (Flavazoles),” Journal of Heterocyclic Chemistry, Vol. 42, No. 2, 2005, pp. 185-189. doi:10.1002/jhet.5570420202

[3]   N. P. Buu-Hoi, J. N. Vallat, G. Saint-Ruf and G. Lambelin, “Chimie, Physico-Chimie et Pharmacologie due Flavazole et de Quelques-Uns de Ses Derives Substitutes,” Chimie Therapeutique, Vol. 6, No. 4, 1971, pp. 245-250.

[4]   Y. Kurasawa, M. Muramatsu, K. Yamazaki, S. Tajima, Y. Okamoto and A. Takada, “A Convenient Synthesis and Antifungal Activity of 1-Aryl-1H- and 1-Aryl-3-het-eroaryl- 1H-pyrazolo [3,4-b]quinoxalines,” Journal of Hetero-cyclic Chemistry, Vol. 23, No. 5, 1986, pp. 1379-1382. doi:10.1002/jhet.5570230524

[5]   Y. Kurasawa, M. Mu-ramatsu, K. Yamazki, S. Tajima, Y. Okamoto and A. Takada, “A facile Synthesis of 1-Aryl-3- het-eroaryl-1H-pyrazolo[3,4-b]quinoxalines and Related Com-pounds with Antifungal Activity,” Journal of Heterocyclic Chemistry, Vol. 23, No. 5, 1986, pp. 1391-1394. doi:10.1002/jhet.5570230527

[6]   M. M. Abbasi, S. M. El-Kousy, Y. E. El-Moghazy and S. El-Kafrawy, “Synthesis of Pyrazoloquinoxaline-C-Acyclic Nucleosides with Expected Antiviral Activity,” International Journal of Chemistry, Vol. 15, No. 2, 2005, pp. 77-84.

[7]   M. A. Ortega, M. E. Montoya, B. Azrranz, A. Jaso, I. Aldana, S. Leclere, L. Meijer and A. Monge, “Pyrazolo [3,4-b]quinoxalines. A New Class of Cy-clin-Dependent Kinases Inhibitors,” Bioorganic and Medicinal Chemistry, Vol. 10, No. 7, 2002, pp. 2177-2184. doi:10.1016/S0968-0896(02)00069-X

[8]   S. Young, M. K. Lee, Y. Kurasawa and A. Takada, “Synthesis and Evaluation of 1H-Pyrazolo[3,4-b]quinoxalines and 1-Aryl-3-quinoxalinyl-1,2,4-triazoles as Antibacterial Agents,” Journal of Heterocyclic Chemistry, Vol. 33, No. 6, 1996, pp. 1855-1858. doi:10.1002/jhet.5570330649

[9]   A. Mongae, J. A. Palop, A. Ochoa de Retana, I. Urbasos and A. E. Fernandez, “New Quinoxalines and Pyrazolo [3,4-b]quinoxalines with An-tihypertensive Activity,” Ana- les de Quimica, Serie C: Quimica Organica y Bioquimica, Vol. 84, No. 3, 1988, pp. 364-366.

[10]   H. Ohle and G. A. Melkonian, “1-Phenyl-3-(D-erythro- trioxypropyl)-flavazol. Die Konstitu-tion der Seitenkette,” Berichte der Deutschen Chemischen Ge-sellschaft, Vol. 74, No. 2, 1941, pp. 279-291. doi:10.1002/cber.19410740220

[11]   M. A. E. Sallam, H. M. El Nahas, S. M. E. Abdel Megid and T. Anthonsen, “1-Aryl-6,7-dichloro-3-β-D-erythro- furano-syl-pyrazolo[3,4-b]quinoxalines C-Nucleoside Ana- logs,” Car-bohydrate Research, Vol. 280, No. 1, 1996, pp. 127-138. doi:10.1016/0008-6215(95)00187-5

[12]   H. Ohle and A. Iltgen, “Flavazole, IV. Mitteil: Die Stamm- verbindung: Das Flavazol,” Berichte der Deutschen Chemischen Gesellschaft, Vol. 76, No. 1-2, 1943, pp. 1-14. doi:10.1002/cber.19430760102

[13]   H. El Khadem, “Chemistry of Osazones,” Advances in Carbohydrate Chemistry, Vol. 20, 1965, pp. 139-181. doi:10.1016/S0096-5332(08)60298-2

[14]   H. Ohle and M. Hielscher, “Nolez zur Konstitution des 1-Phenyl-d-fructosons,” Berichte der Deutschen Chemischen Gesellschaft, Vol. 74, No. 1, 1941, pp. 18-19. doi:10.1002/cber.19410740105

[15]   B. Nordin, “1-Phenyl Flavazoles,” In: R. L. Whitler, M. L. Wolfrom and J. N. Bemil-ler, Eds., Methods in Carbohydrate Chemistry, Academic Press, New York, 1963, pp. 136-137.

[16]   R. Lohmar and K. P. Link, “Note on the Reaction of d-Glucosamine with o-Phenylene Diamine,” The Journal of Biological Chemistry, Vol. 150, 1943, pp. 351-352.