New 1H-1-alkyl-6-methyl-3-phenyl-7-phenylazo-pyrazolo[5,1-c][1,2,4]triazoles through regioselective alkylation of 1H-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles

• Authors: Vasile-Nicolae Bercean , Valentin Badea , Călin Deleanu , Alina Nicolescu
• Languages of publication: EN

Abstracts

EN

1H-1-Alkyl-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles (2aa-ad) were obtained by regioselective alkylation of 1H-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles (2a). 1H-1-Alkyl-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles 2aa and 2ab were also prepared by coupling phenyldiazonium chloride with 1H-1-alkyl-6-methyl-3-phenyl-pyrazolo[5,1-c][1,2,4]triazoles 1aa and 1ab. The new compounds were characterized by IR, UV-VIS, 1H-NMR, 13C-NMR, and 15N-NMR spectroscopy and their structures and actual tautomeric forms were established unequivocally. [...]

Keywords

EN

Pyrazolo[5,1-c][1,2,4]triazole; Regioselective N-alkylation; Azo compound; Tautomerism

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 2
• Pages: 373-379

Dates

published

1 - 4 - 2012

online

29 - 1 - 2012

Contributors

author

Vasile-Nicolae Bercean

• Department of Applied Chemistry and Engineering of Organic and Natural Compounds, Faculty of Industrial Chemistry and Environmental Engineering, “Politehnica” University Timişoara, RO-300001, Timişoara, Romania

author

Valentin Badea

• Department of Applied Chemistry and Engineering of Organic and Natural Compounds, Faculty of Industrial Chemistry and Environmental Engineering, “Politehnica” University Timişoara, RO-300001, Timişoara, Romania

author

Călin Deleanu

author

Alina Nicolescu

References

• [1] J. Bailey, J. Chem. Soc. Perk. T. 1, 18, 2047 (1977) http://dx.doi.org/10.1039/p19770002047[Crossref]
• [2] J. Bailey, E. Bowes, P.A. Marr, GB 1247493 (Eastman Kodak Co., USA, 1967)
• [3] D. R. Diehl, K. Mbiya, S.W. Cowan, EP 1014185 (Eastman Kodak Co., USA, 1999)
• [4] K. Tawara, O. Akira, EP 0763569A1 (Konica Co., Japan, 1997)
• [5] G. Plos, A. Lagrange, EP 1062937 (L’Oreal, France, 2000)
• [6] M. Andousset, EP 1040818 (L’Oreal, France, 2000)
• [7] K. Katsunori, S. Takayuki, I. Hiromi, JP 167305 (Konica Co., Japan, 2002)
• [8] M.A. Abdallah, S.M. Riyadh, I.M. Abbas, S.M. Gomha, J. Chin. Chem. Soc-Taip. 52, 987 (2005) [Crossref]
• [9] J. Deschamps, J. Arriau, P. Parmentier, Tetrahedron 27(23), 5779 (1971) http://dx.doi.org/10.1016/S0040-4020(01)91745-4[Crossref]
• [10] J. Arriau, J. Deschamps, J. Teysseyre, A. Maquestiau, Y. van Haverbeke, Tetrahedron 30(10), 1225 (1974) http://dx.doi.org/10.1016/S0040-4020(01)97294-1[Crossref]
• [11] J. Elguero, C. Marzin, A.R. Katritzky, P. Linda, The Tautomerism of Heterocycles (Academic Press, New York, 1976)
• [12] V.I. Minkin, A.D. Garnovskii, J. Elguero, A.R. Katritzky, O.V. Denisko, Adv. Heterocycl. Chem. 76, 157 (2000) http://dx.doi.org/10.1016/S0065-2725(00)76005-3[Crossref]
• [13] I. Alkorta, J. Elguero, J.F. Liebman, Struct. Chem. 17(4), 439 (2006) http://dx.doi.org/10.1007/s11224-006-9065-6[Crossref]
• [14] J.-P. Fayet, M.-C. Vertut, R.M. Claramunt, J.M. Fabrega, L. Knutsson, B. Soc. Chim. Fr. 1–2, 393 (1975)
• [15] R. Faure, E.-J. Vincent, R.-M. Claramunt, J. Elguero, Org. Magn. Resonance 9(9), 508 (1977) http://dx.doi.org/10.1002/mrc.1270090904[Crossref]
• [16] V. Bercean, V. Badea, R. Iorga, C. Csunderlik, Rev. Chim.-Bucharest 54(6), 533 (2003)
• [17] V. Badea, M.D. Şofei, M.M. Venter, V.N. Bercean Tetrahedron, 63, 1467 (2007) http://dx.doi.org/10.1016/j.tet.2006.11.067[Crossref]
• [18] A.R. Katritzky, W. Kuzmierkiewicz, J. Greenhill, Recl. Trav. Chim. Pay-B. 110, 369 (1991) http://dx.doi.org/10.1002/recl.19911100903[Crossref]

Identifiers

DOI

10.2478/s11532-011-0151-2