A method has been developed for the synthesis of 1-adamantyl-3,4,5-R1,R2,R3-pyrazoles by the reaction of 1,3-dehydroadamantane with N-unsubstituted 3,4,5-R1,R2,R3-1H-pyrazoles in an inert solvent. The effect of the NH acidity (pKa) of the starting 3,4,5-R1,R2,R3-1H-pyrazole on the course of the reaction and the product yields was studied.
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L. Wanka, K. Iqbal, and P. R. Schreiner, Chem. Rev., 113, 3516 (2013).
D. Gully, M. Canton, R. Boigegrain, F. Jeanjean, J. C. Molimard, M. Poncelet, C. Gueudet, M. Heaulme, R. Leyris, and A. Brouard, Proc. Natl. Acad. Sci. U.S.A., 90, 65 (1993).
R. M. Myers, J. W. Shearman, M. O. Kitching, A. Ramos-Montoya, D. E. Neal, and S. V. Ley, ACS Chem. Biol., 4, 503 (2009).
D. Gully, B. Labeeuw, R. Boigegrain, F. Oury-Donat, A. Bachy, M. Poncelet, R. Steinberg, M. F. Suaud-Chagny, V. Santucci, N. Vita, F. Pecceu, C. Labbé-Jullié, P. Kitabgi, P. Soubrié, G. L. Fur, and J. P. Maffrand, J. Pharmacol. Exp. Ther., 280, 802 (1997).
B. Labeeuw, D. Gully, F. Jeanjean, J.-C. Molimard, and R. Boigegrain, WO Pat. Appl. 1996032382.
N. Vita, F. Oury-Donat, P. Chalon, M. Guillemot, M. Kaghad, A. Bachy, O. Thurneyssen, S. Garcia, C. Poinot-Chazel, P. Casellas, P. Keane, G. Le Fur, J.-P. Maffrand, P. Soubrie, D. Caput, and P. Ferrara, Eur. J. Pharmacol., 360, 265 (1998).
K. W. Anderson, N. Fotouhi, P. Gillespie, R. A. Goodnow, K. R. Guertin, N.-E. Haynes, M. P. Myers, S. L. Pietranico-Cole, L. Qi, P. L. Rossman, N. R. Scott, K. C. Thakkar, J. W. Tilley, and Q. Zhang, US Pat. Appl. 20070225280A1.
N. V. Makarova, E. I. Boreko, I. K. Moiseev, N. I. Pavlova, S. N. Nikolaeva, M. N. Zemtsova, and G. V. Vladyko, Khim.-Farm. Zh., 36, No. 1, 5 (2002). [Pharm. Chem. J., 36, 3 (2002).]
V. V. Zarubaev, E. L. Golod, P. M. Anfimov, A. A. Shtro, V. V. Saraev, A. S. Gavrilov, A. V. Logvinov, and O. I. Kiselev, Bioorg. Med. Chem., 18, 839 (2010).
R. Spano, G. Linari, and R. Marri, J. Med. Chem., 13, 554 (1970).
S. Höpner, K. Dickhaut, M. Hofstätter, H. Krämer, D. Rückerl, J. A. Söderhäll, S. Gupta, V. Marin-Esteban, R. Kühne, C. Freund, G. Jung, K. Falk, and O. Rötzschke, J. Biol. Chem., 281, 38535 (2006).
V. G. Tsypin, M. S. Pevzner, and E. L. Golod, Zh. Org. Khim., 37, 1843 (2001). [Russ. J. Org. Chem., 37, 1762 (2001).]
A. S. Gavrilov, E. L. Golod, V. V. Kachala, and B. I. Ugrak, Zh. Org. Khim., 37, 1822 (2001). [Russ. J. Org. Chem., 37, 1741 (2001).]
P. Cabildo, R. M. Claramunt, I. Forfar, and J. Elguero, Tetrahedron Lett., 35, 183 (1994).
P. Cabildo, R. M. Claramunt, D. Sanz, M. C. Foces-Foces, F. Hernández-Cano, J. P. Fayet, M. C. Vertut, and J. Elguero, J. Heterocycl. Chem., 23, 1045 (1986).
P. Cabildo, R. M. Claramunt, and J. Elguero, J. Heterocycl. Chem., 21, 249 (1984).
G. M. Butov, V. M. Mokhov, G. Yu. Parshin, and E. A. Kamneva, Izv. Volg. State Technical Univ., 8, No. 2, 6 (2011).
V. M. Mokhov, G. M. Butov, and S. V. D'yakonov, Izv. Volg. State Technical Univ., 9, No. 5, 6 (2012).
V. M. Mokhov, G. M. Butov, and B. A. Lysykh, Izv. Volg. State Technical Univ., 10, No. 4, 21 (2013).
G. M. Butov, V. M. Mokhov, G. Yu. Parshin, and O. A. Panyushkina, Zh. Org. Khim., 45, 1736 (2009). [Russ. J. Org. Chem., 45, 1732 (2009)].
G. M. Butov, V. M. Mokhov, G. Yu. Parshin, B. A. Lysykh, L. D. Konyushkin, and S. I. Firgang, Zh. Org. Khim., 47, 150 (2011). [Russ. J. Org. Chem., 47, 150 (2011)].
G. M. Butov, V. M. Mokhov, G. Yu. Parshin, and O. A. Panyushkina, RU Pat., No. 2280032; Byul. Izobr. No. 20 (2006).
J. Catalan and J. Elguero, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 41, Academic Press (1987), p. 187.
R. E. Pincock, J. Schmidt, W. B. Scott, and E. J. Torupka, Can. J. Chem., 50, 3958 (1972).
B. Lee, P. Kang, K. H. Lee, J. Cho, W. Nam, W. K. Lee, and N. H. Hur, Tetrahedron Lett., 54, 1384 (2013).
J. P. H. Juffermans and C. L. Habraken, J. Org. Chem., 51, 4656 (1986).
A. A. Zaitsev, I. O. Kortusov, I. L. Dalinger, V. V. Kachala, G. P. Popova, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2054 (2009). [Russ. Chem. Bull., 58, 2118 (2009).]
I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, G. P. Popova, and S. A. Shevelev, Mendeleev Commun., 22, 43 (2012).
This work was carried out with the financial support of the Russian Ministry of Education and published as the results of the Third International Conference "New Trends in the Chemistry of Heterocyclic Compounds" (17-21 September 2013, Pyatigorsk, Russia).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 816-820, May, 2014.
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Butov, G.M., Lysykh, B.A., Dalinger, I.L. et al. Synthesis of 1-Adamantyl-3,4,5-R1,R2,R3-Pyrazoles. Chem Heterocycl Comp 50, 752–756 (2014). https://doi.org/10.1007/s10593-014-1530-3
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DOI: https://doi.org/10.1007/s10593-014-1530-3