1-(Cyanoacetyl)-3,5-dimethylpyrazole reacted with 2-cyanoacrylamides in the presence of triethylamine with the formation of triethylammonium salts of 4-monosubstituted-2,6-dioxopiperidine-3,5-di-carbonitriles (Guareschi imides) or the products of their oxidation, the 4-aryl-3,5-dicyano-6-oxo-1,6-di-hydropyridin-2-olates.
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References
I. Guareschi, Chem. Zbl., 72, Pt. I, 579 (1901).
E. Grande, E. Quenda, A. Pasquali, L. Sabbatini, and I. Guareschi, J. Chem. Soc., Abstr., 74, 272 (1898).
I. Guareschi, Chem. Zbl., 69, Pt. II, 544 (1898).
I. Guareschi and E. Grande, Chem. Zbl., 70, Pt. 2, 439 (1899).
I. Guareschi, Gazz. Chim. Ital., 49 (I), 126 (1919).
F. H. Shaw, S. R. Simon, N. Cass, A. Shulman, J. R. Anstee, and E. R. Nelson, Nature, 174, 402 (1954).
A. Shulman, F. H. Shaw, N. Cass, and N. M. Whyte, Brit. Med. J., 1, 1238 (1955).
T. C. Somers, Nature, 178, 996 (1956).
E. Tagmann, E. Sury, and K. Hoffman, Helv. Chim. Acta, 35, 1235 (1952).
E. Tagmann, F. Sury, and K. Hoffman, Helv. Chim. Acta, 35, 1541 (1952).
G. J. Handley, E. R. Nelson, and T. C. Somers, Aust. J. Chem., 13, 129 (1960).
S. M. McElvain and D. H. Clemens, J. Am. Chem. Soc., 80, 3915 (1958).
T. C. Bruice and W. C. Bradbury, J. Am. Chem. Soc., 87, 4838 (1965).
A. A. Liebman and F. E. Digangi, J. Pharm. Sci., 52, 395 (1963).
R. W. Holder, J. P. Daub, W. E. Baker, R. H. Gilbert III, and N. A. Graf, J. Org. Chem., 47, 1445 (1982).
P. Jimonet, Y. Ribeill, G. A. Bohme, A. Boireau, M. Cheve, D. Damour, A. Doble, A. Genevois-Borella, F. Herman, A. Imperato, S. Le Guern, F. Manfre, J. Pratt, J. C. R. Randle, J.-M. Sutzmann, and S. Mignani, J. Med. Chem., 43, 2371 (2000).
S. A. El Batran, A. E. N. Osman, M. M. Ismail, and A. M. El Sayed, Inflammopharmacology, 14, 62 (2006).
N. Palit, J. Indian Chem. Soc., 14, 219 (1937).
W. Liqiang, Y. Chunguang, Y. Liming, and Y. Lijuan, Heterocycles, 78, 977 (2009).
S. Checchi, L. P. Vettori, and F. Bruni, Farmaco, Ed. Sci., 35, 120 (1980).
G. N. Walker, J. Org. Chem., 37, 3955 (1972).
B. Nguyen, K. Chernous, D. Endlar, B. Odell, M. Piacenti, J. M. Brown, A. S. Dorofeev, and A. V. Burasov, Angew. Chem., Int. Ed., 46, 7655 (2007).
I. Guareschi, Atti R. Accad. Sci. Torino, 32, 565 (1897).
J. N. E. Day and J. F. Thorpe, J. Chem. Soc., 117, 1465 (1920).
J. L. Soto, A. Lorente, and L. Fuentes, An. Quim., 74, 648 (1978).
J. S. A. Brunskill, J. Chem. Soc. C, 960 (1968).
G. Dietz, W. Fiedler, and G. Faust, Chem. Ber., 102, 4147 (1969).
J. S. A. Brunskill, J. Chem. Soc., Perkin Trans. I, 2946 (1972).
C. N. O'Callaghan, Proc. R. Ir. Acad., Sect. B, 77, 533 (1977).
N. M. Fathy and G. H. Elgemeie, J. Chem. Eng. Data, 33, 218 (1988).
V. P. Litvinov, Usp. Khim., 72, 75 (2003). [Russ. Chem. Rev., 72, 69 (2003).]
V. P. Litvinov, Usp. Khim., 75, 645 (2006). [Russ. Chem. Rev., 75, 577 (2006).]
E. Chigorina and V. Dotsenko, in: Proc. 15 th Int. Electron. Conf. Synth. Org. Chem., 1–30 Nov. 2011. Sciforum Electronic Conferences Series, 2011. Avail. URL: http://www.sciform.net/presentation/702/
E. A. Chigorina, V. V. Dotsenko, and S. G. Krivokolysko, Khim. Geterotsikl. Soedin., 1108 (2011). [Chem. Heterocycl. Compd., 47, 913 (2011)].
V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2397 (2007). [Russ. Chem. Bull., Int. Ed., 56, 2482 (2007)].
V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Monatsh. Chem., 138, 607 (2007).
K. A. Frolov, V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 471 (2012). [Chem. Heterocycl. Compd., 48, 442 (2012)].
N. Y. Gorobets, B. N. Yousefi, F. Belaj, and C. O. Kappe, Tetrahedron, 60, 8633 (2004).
E. A. Chigorina and V. V. Dotsenko, Khim. Geterotsikl. Soedin., 1216 (2012). [Chem. Heterocycl. Compd., 48, 1133 (2012)].
S. G. Krivokolysko, Diss. Dokt. Khim. Nauk, Moscow (2001).
S. G. Krivokolysko, V. D. Dyachenko, E. B. Rusanov, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 525 (2001). [Chem. Heterocycl. Compd., 37, 477 (2001)].
L. A. Donders, F. A. A. M. De Leeuw, and C. Altona, Magn. Reson. Chem., 27, 556 (1989).
V. V. Dotsenko, S. G. Krivokolysko, E. B. Rusanov, A. V. Gutov, and V. P. Litvinov, Izv. Akad. Nauk , Ser. Khim., 1417 (2007). [Russ. Chem. Bull., Int. Ed., 56, 1470 (2007)].
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 615–627, April, 2013.
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Chigorina, E.A. 1-(Cyanoacetyl)-3,5-dimethylpyrazole as an effective alternative to cyanoacetic ester in the synthesis of 2,6-dioxopiperidine-3,5-dicarbonitrile derivatives. Chem Heterocycl Comp 49, 574–585 (2013). https://doi.org/10.1007/s10593-013-1284-3
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DOI: https://doi.org/10.1007/s10593-013-1284-3