Abstract
The reaction of 5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine with α,β-unsaturated carbonyl compounds in MeOH in the presence of MeONa affords partially hydrogenated aryl-substituted [1,2,4]triazolo[5,1-b]quinazolines. Hydrolysis, oxidation, reduction, and alkylation of 5,6,8-triphenyl-5,6,7,10-tetrahydro[1,2,4]triazolo[5,1-b]quinazoline were studied. The structure of one oxidation product, viz., 7-hydroxy-5,6,8-triphenyl-6,7-dihydro[1,2,4]triazolo[5,1-b]quinazoline, was established by X-ray diffraction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Kh. M. Shakhidoyatov, in Azotistye geterotsikly i alkaloidy [Nitrogen Heterocycles and Alkaloids], Iridium-Press, Moscow, 2001, 186 (in Russian).
WO Pat 9833792; Chem Abstr., 1998, 129, 161568p.
A. Deussen, M. Stappert, S. Schäfer, and M. Kelm, Circulation, 1999, 99, 2041.
G. H. Elgemeie, N. M. Fathy, and D. A. Farrag, Egypt. J. Pharm. Sci., 1997, 38, 351.
J. Reiter and K. Esses-Reiter, J. Heterocycl. Chem., 1991, 28, 561.
J. Reiter, G. Berecz, and I. Pallagi, J. Heterocycl. Chem., 1991, 28, 721.
E. Rivo and J. Reiter, J. Heterocycl. Chem., 1992, 29, 1189.
G. Berecz and J. Reiter, J. Heterocycl. Chem., 1999, 36, 1199.
S. M. Desenko, Kh. M. Estrada, V. D. Orlov, and O. A. Ponomarev, Khim. Geterotsikl. Soedin., 1991, 105 [Chem. Heterocycl. Compd., 1991, 27 (Engl. Transl.)].
S. M. Desenko, V. D. Orlov, N. V. Getmanskii, O. V. Shishkin, S. V. Lindeman, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 1994, 481 [Chem. Heterocycl. Compd., 1994, 30 (Engl. Transl.)].
O. V. Shishkin, P. N. Abakumov, S. M. Desenko, N. V. Getmanskii, and V. D. Orlov, Kristallografiya, 1998, 43, 39 [Crystallogr. Repts, 1998, 43 (Engl. Transl.)].
V. V. Lipson, S. M. Desenko, M. G. Shirobokova, and V. V. Borodina, Khim. Geterotsikl. Soedin., 2003, 1383 [Chem. Heterocycl. Compd., 2003, 39 (Engl. Transl.)].
K.-J. Lee, S. H. Kim, S. Kim, H. Park, Y. R. Cho, B. Y. Chung, and E. E. Schweizer, Synthesis, 1994, 1057.
D. S. Khachatryan and K. R. Matevosyan, in Azotistye geterotsikly i alkaloidy [Nitrogen Heterocycles and Alkaloids], Iridium-Press, Moscow, 2001, 558 (in Russian).
V. V. Lipson, I. V. Ignatenko, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, S. A. Komykhov, N. V. Logvinenko, V. D. Orlov, and H. Meier, J. Heterocycl. Chem., 2003, 40, 1081.
S. M. Desenko, V. D. Orlov, and V. V. Lipson, Khim. Geterotsikl. Soedin., 1990, 1638 [Chem. Heterocycl. Compd., 1990, 26 (Engl. Transl.)].
N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya, J. Phys. Org. Chem., 1990, 3, 147.
S. M. Desenko, O. V. Shishkin, V. D. Orlov, V. V. Lipson, S. V. Lindeman, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 1994, 981 [Chem. Heterocycl. Compd., 1994, 30 (Engl. Transl.)].
C. Weygand, Organisch-Chemische Experimentierkunst, Zweite Verbesserte Auflage, Leipzig, 1948, 715 ss.
Weygand-Hilgetag, Organisch-Chemische Experimentierkunst, Verlag, Leipzig, 1964, 944 ss.
Dictionary of Organic Compounds, Eds I. Heilbron and H. M. Bunbury, 1949, Vol. 1.
G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Rev. 5.1, Siemens Analytical X-ray Instruments Inc. (Germany), 1998.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 335—340, February, 2006.
Rights and permissions
About this article
Cite this article
Lipson, V.V., Desenko, S.M., Ignatenko, I.V. et al. Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines. Russ Chem Bull 55, 345–350 (2006). https://doi.org/10.1007/s11172-006-0258-3
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0258-3