Ethyl 5-amino-3-oxo-1,2-dihydro-1H-pyrazole-1-carboxylate undergoes selective cyclocondensation with 1,3-dicarbonyl compounds or their synthetic equivalents to give ethyl 3-oxo-1,2-dihydro-pyrazolo[3,4-b]pyridine-1-carboxylates which are readily converted to their 1-unsubstituted analogs.
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E. G. Paronikyan, S. N. Sirikanyan, A. S. Noravyan, R. G. Paronikyan, and I. A. Dzhagatspanyan, Khim.-Farm. Zh., 35, No. 1, 9 (2001).
R. M. Schelkun and P.-W. Yuen, US Pat. Appl. 2006116376.
M. Manpadi, P. Y. Uglinskii, S. K. Rastogi, K. M. Cotter, Y.-S. C. Wong, L. A. Anderson, A. J. Ortega, S. Slambrouck, W. F. A. Steelant, S. Rogelj, P. Tongwa, M. Y. Antipin, I. V. Magedov, and A. Kornienko, Org. Biomol. Chem., 5, 3865 (2007).
G. Zoller, S. Petry, G. Muller, H. Heuer, and K.-H. Bar-Inghaus, WO Pat. Appl. 2005073199.
G. Zoller, S. Petry, G. Muller, H. Heuer, and K.-H. N. Tennagels, US Pat. Appl, 2008287448.
A. Chandra Sheker Reddy, B. Narsaiah, and R. V. Venkataratnam, Synth. Commun., 27, 2217 (1997).
Z. A. Kalme, B. Roloff, Yu. E. Pelcher, Yu. Yu. Popelis, F. Hagen, and G. J. Duburs, Khim. Geterotsikl. Soedin., 1218 (1992). [Chem. Heterocycl. Compd., 28, 1031 (1992)].
R. Balicki, Pol. J. Chem., 57, 1251 (1983).
P. Papini, S. Checchi, and M. Ridi, Gazz. Chim. Ital., 87, 931 (1957).
J.-L. Imbach, R. Jacquier, and J.-L. Vidal, Bull. Soc. Chim. Fr., 1929 (1970).
R. Balicki and P. Nantka-Nemirski, Pol. J. Chem., 54, 2175 (1980).
E. C. Taylor and J. W. Barton, J. Am. Chem. Soc., 81, 2448 (1959).
W. Ried and E. U. Kocher, Justus Liebigs Ann. Chem., 647, 116 (1961).
G. Zoller, S. Petry, G. Muller, H. Hever, and K.-H. N. Tennagels, WO Pat. Appl. 2007110216.
R. Balicki, Pol. J. Chem., 56, 711 (1982).
P. Papini, S. Checchi, and M. Ridi, Gazz. Chim. Ital., 84, 769 (1954).
B. Graham, H. D. Porter, and A. Weissberger, J. Am. Chem. Soc., 71, 983 (1949).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 390-394, February, 2012.
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Lebedˈ, P.S., Mozgovaya, N.G., Kos, P.O. et al. Ethyl 5-amino-3-oxo-1,2-dihydro-1H-pyrazole-1-carboxylate in the selective synthesis of partially hydrogenated pyrazolo[3,4-b]pyridin-3-ones. Chem Heterocycl Comp 48, 368–371 (2012). https://doi.org/10.1007/s10593-012-0999-x
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DOI: https://doi.org/10.1007/s10593-012-0999-x