We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and С-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine.
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Danagulyan, G. G.; Boyakhchyan, A. P.; Danagulyan, A. G.; Panosyan, H. A. Chem. Heterocycl. Compd. 2011, 47, 321. [Khim. Geterotsikl. Soedin. 2011, 393.]
Danagulyan, G. G.; Boyakhchyan, A. P.; Tumanyan A. K.; Danagulyan, A. G.; Kirakosyan V. G. Chem. Heterocycl. Compd. 2011, 47, 386. [Khim. Geterotsikl. Soedin. 2011, 465.]
Shirakawa, K. Yakugaku Zasshi 1958, 78, 1395; Chem. Abstr. 1959, 53, 8150e.
Allen, C. F. H.; Beilfuss, H. R.; Burness, D. M.; Reynolds, G. A.; Tinker, J. F.; Van Allan, J. A. J. Org. Chem. 1959, 24, 787.
Danagulyan, G. G.; Tadevosyan, D. A.; Tamazyan, R. A.; Panosyan, G. A. Chem. Heterocycl. Compd. 2006, 42, 233. [Khim. Geterotsikl. Soedin. 2006, 262.]
Danagulyan, G. G.; Tumanyan, A. K.; Attaryan, O. S.; Danagulyan, A. G.; Chupakhin, O. N. Khim. Zh. Armenii 2014, 67(1), 85.
Danagulyan, G. G.; Sahakyan, L. G.; Katritzky, A. R.; Denisenko, S. N. Heterocycles 2000, 53, 419.
Danagulyan, G. G. Chem. Heterocycl. Compd. 2005, 41, 1205. [Khim. Geterotsikl. Soedin. 2005, 1445.]
Danagulyan, G. G.; Saakyan, L. G., Panosyan G. A. Chem. Heterocycl. Compd. 2001, 37, 323. [Khim. Geterotsikl. Soedin. 2001, 351.]
Danagulyan, G. G.; Panosyan, G. A.; Sahakyan, L. G. Chem. Heterocycl. Compd. 2007, 43, 996. [Khim. Geterotsikl. Soedin. 2007, 1175.]
Attaryan, O. S.; Grigoryan, A. J.; Panosyan, G. A.; Matsoyan, S. G. Khim. Zh. Armenii 2001, 54(1–2), 102.
Rstakyan, V. I.; Hakobyan, A. E.; Zakaryan, G. B.; Hayotsyan, S. S.; Attaryan, H. S.; Asratyan, G. V. Russ. J. Gen. Chem. 2014, 84, 1641. [Zh. Obsch. Khim. 2014, 84, 1397.]
Attaryan, O. S.; Baltayan, A. O.; Matsoyan, S. G. Russ. J. Gen. Chem. 2007, 77, 297. [Zh. Obsch. Khim. 2007, 77, 325.]
Katritzky, A. R.; Kuzmierkiewicz, W.; Greenhill, J. V. Rec. Trav. Chim. Pays-Bas 1991, 110(9), 369.
Nagao, Y.; Sano, S.; Ochiai, M.; Fujita, E. Tetrahedron 1990, 46, 3211.
Srivastava, S. K.; Srivastava, S.; Srivastava, S. D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2002, 41, 1937.
Sagitullin, R. S.; Kost, A. N.; Danagulyan, G. G. Tetrahedron Lett. 1978, 19, 4135.
Badalyan, K. S.; Asratyan, A. G.; Attaryan, O. S. Russ. J. Gen. Chem. 2012, 82, 946. [Zh. Obsch. Khim. 2012, 82, 876.]
North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1968, A24, 351.
Sheldrick, G. M. SHELXTL-97, Program for X-ray Crystal Structure Solution; Göttingen University: Göttingen, 1997.
This work was performed within the framework of Russian-Armenian grant 13RF-087 by the State Committee for Science at the Ministry of Education and Science, Republic of Armenia and the Russian Foundation for Basic Research, as well as with financial support from the State Committee for Science at the Ministry of Education and Science, Republic of Armenia (grant 13-1D334).
NMR spectra were acquired at the Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia (program US CRDF RESC 17–5).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(5), 483–490
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Danagulyan, G.G., Tumanyan, A.K., Attaryan, O.S. et al. Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts. Chem Heterocycl Comp 51, 483–490 (2015). https://doi.org/10.1007/s10593-015-1724-3
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DOI: https://doi.org/10.1007/s10593-015-1724-3