Abstract
The first representatives of pyrazolines were synthesized in the last century. These nitrogen-containing heterocyclic compounds became important in the development of different bioactive substances. For this reason, various procedures have been worked out for their synthesis. In the present article we summarize those synthetic methods providing 1- or 2-pyrazolines by the reactions of α,β-unsaturated ketones with diazomethane or hydrazine derivatives.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
E. Fischer and O. Knövenagel, Ann.,239, 194 (1887).
K. v. Auwers and K. Müller, Ber.,41, 4230 (1908).
K. v. Auwers and A. Kreuder, Ber.,58, 1974 (1925).
K. v. Auwers and E. Cauer E., Ann.470, 284 (1929).
K. v. Auwers and F. König, Ann.,496, 27 (1932).
K. v. Auwers and O. Ungemach, Chem. Ber.,66, 1198 (1933).
K. v. Auwers and O. Ungemach, Chem. Ber.,66, 1205 (1933).
E. P. Kohler and L. L. Steele, J. Am. Chem. Soc.41, 1093 (1919).
L. I. Smith and W. B. Pings, J. Org. Chem.,2, 23 (1937).
W. M. Jones, J. Am. Chem. Soc.,81, 5153 (1959).
W. M. Jones and W. T. Tai, J. Org. Chem.,27, 1324 (1962).
C. G. Overberger and J. P. Anselme, J. Am. Chem. Soc.,84, 869 (1962).
T. V. Van Anken and K. L. Rinehart, Jr., J. Am. Chem. Soc.,84, 3736 (1962).
G. D. Kennedy, A. L. Baumstark, M. Dotrong, T. Thomas, and N. Narayanan, J. Heterocycl. Chem.,28, 1773 (1991).
K. Ramalingam, G. X. Thyvekikakath, K. D. Berlin, R. W. Chesnut, R. A. Brown, N. N. Durham, A. E. Ealick, and D. van der Helm, J. Med. Chem.,20, 847 (1977).
J. G. Lombardino and I. G. Otterrness, J. Med. Chem.,830 (1981).
U. S. Pat. 3,624,102; R. E. Brown and J. Shavrel, Jr.; Chem. Abs.,76, 59618 (1972).
A. Weissberger, The Chemistry of Heterocyclic Compounds, Vol. 22, Wiley, New York (1967), p. 180.
H. v. Pechmann, Ber.,27, 1890 (1894).
E. Bergmann and F. J. Bergmann, Org. Chem.,3, 125 (1938).
A. N. Nesmeyanov and N. K. Kochetkov, Izv. Akad Nauk SSSR, Otd. Khim Nauk., 686 (1951).
L. N. Owen and M. V. S. Sultanbawa, J. Chem. Soc., 3098 (1949).
S. Y. Spencer and G. F. Wright, J. Am. Chem. Soc.,63, 2014 (1941).
J. Azzarello, Gazz. Chim. Ital.,36, 50 (1906).
L. I. Smith and K. L. Howard, J. Am. Chem. Soc.,65, 165 (1943).
G. V. S. Raju and K. S. Rao, Curr. Sci.,58, 1030 (1989).
A. Lévai and G. Tóth, Trends in Heterocyclic Chemistry,4, 89 (1995).
S. G. Ghate, R. Kaushal, and S. S. Deshapande, J. Indian Chem. Soc.,27, 633 (1950).
A. Mustafa and A. M. Fleifel, J. Org. Chem.,24, 1470 (1959).
G. H. Sayed and N. Kjosen, Indian J. Chem.,19B, 980 (1980).
L. A. Aleksandrova, N. A. Dorofeeva, A. V. Chernova, and V. K. Khairullin, Zh. Org. Khim.,14, 1974 (1978).
A. L. Tökés, A. Szöllösy, G. Tóth, and A. Lévai, Acta Chim. Hung.,112, 335 (1983).
A. Lévai, Monatsh. Chem.,126, 1245 (1995).
A. Lévai, Z. Cziáky, J. Jekö, and Z. Szabó, Indian J. Chem.,35B, 1091 (1996).
A. Mustafa and M. K. Hilmy, J. Chem. Soc., 3254 (1951).
J. Kamecki, W. Perka, and L. Pijewska, Polish J. Chem.,59, 285 (1985).
L. Pijewska, J. Kamecki, and W. Perka-Karolczak, Pharmazie.,48, 254 (1993).
G. Tóth, A. Szöllösy, A. Lévai, and G. Kotovych, J. Chem. Soc. Perkin Trans. II, 1895 (1986).
G. Tóth, A. Lévai, and H. Duddeck, Magn. Reson. Chem.,30, 235 (1992).
G. Tóth, A. Lévai, A. Szöllösy, and H. Duddeck, Tetrahedron,49, 863 (1993).
K. v. Auwers and H. Voss, Ber.,42, 4411 (1909).
N. Kishner and J. Russ. Phys. Chem. Soc.,45, 949 (1913).
K. v. Auwers and P. Heimke, Ann.458, 186 (1927).
K. v. Auwers and E. Lömmerhirt, Ber.,54, 1000 (1921).
L. C. Raiford and J. B. Entrikin, J. Am. Chem. Soc.,55, 1125 (1933).
L. C. Raiford and W. J. Peterson, J. Org. Chem.,1, 544 (1936).
H. B. Nisbert, J. Chem. Soc., 1237 (1938).
L. C. Raiford and G. V. Gundy, J. Org. Chem.,3, 265 (1938).
R. H. Wiley, C. H. Jarboe, F. N. Hayes, E. Hansbury, J. T. Nielsen, P. X. Callahan, and M. C. Sellars, J. Org. Chem.,23, 732 (1958).
P. Venturella, A. Bellino, and S. Cusmano, Ann. Chim. (Rome),51, 34 (1961).
D. G. Pereyaslova, V. E. Bondarenko, and B. M. Krasovitskii, Khim. Geterotsikl. Soed., No. 1, 114 (1969).
S. P. Sachchar and A. K. Singh, J. Indian Chem. Soc.,62, 142 (1985).
C. Gao and A. S. Hay, Synth. Commun.,25, 1877 (1995).
A. S. R. Anjaneyulu, Rani G. Sudha, Annapurna K. Gowri, K. Mallavadhani, and Y. L. N. Murthy, Indian J. Chem.,34B, 933 (1995).
S. A. Basaif, H. A. Albar, and H. M. Faidallah, Indian J. Heterocycl. Chem.,5, 121 (1995).
O. M. O. Habib, A. M. Khalil, E. M. Kandeel, and E. B. Abdalla, Rev. Roum. Chim.,31, 629 (1986).
A. E. A. Sammour, Tetrahedron.,20, 1067 (1964).
H. Ferres, M. S. Hamdam, and W. R. Jackson, J. Chem. Soc. (B)., 1892 (1971).
Y. A. Al-Farkh, F. H. Al-Hajjar, F.S. Al-Shamali, and H. S. Hammond, Chem. Pharm. Bull.,27, 257 (1979).
N. Bauer and H. Dieterle, Ber.,44, 2697 (1911).
N. Kishner, J. Russ. Phys. Chem.,47, 1819 (1915).
F. Straus, Ber.,51, 1457 (1918).
E. P. Kohler and L. L. Steele, J. Am. Chem. Soc.,41, 1105 (1919).
L. C. Raiford and R. H. Manley, J. Org. Chem.,5, 590 (1940).
K. Freudenberg and W. Stoll, Ann.,440, 38 (1924).
F. G. Weber, K. Brosche, C. Seedorf, and A. Rinow, Monatsh. Chem.,100, 1924 (1969).
M. G. Joshi and K. N. Wadodkar, Indian J. Chem.,20B, 1090 (1981).
T. C. Sharma, S. R. Pawar, and N. I. Reddy, Acta Chim. Hung.,112, 159 (1983).
B. S. Holla and K. V. Udupa, Indian J. Chem.,29B, 887 (1990).
O. Widman, Ber.,49, 477 (1916).
O. Widman, Ber.,49, 2778 (1916).
H. Jörlander, Ber.,49, 2782 (1916).
S. Bodforss, Ber.,49, 2795 (1916).
S. Bodforss, Ber.,51, 192 (1918).
G. Litkei, A. Neubauer, and R. Bognár, Magy. Kém. Foly.,78, 359 (1972).
A. Neubauer, G. Litkei, and R. Bognár, Tetrahedron.,28, 3241 (1972).
K. M. Ghoniem, M. M. Badran, M. A. Shaaban, and S. El-Meligie, Egypt J. Pharm. Sci.,29, 563 (1988).
C. Dupuy and J. J. Luche, Tetrahedron.,45, 3437 (1989).
F. Kállay, G. Janzsó, and I. Koczor, Tetrahedron.,21, 19 (1965).
F. Kállay, G. Janzsó, and I. Koczor Tetrahedron.,21, 3037 (1965).
F. Kállay, G. janzsó, and I. Koczor, Tetrahedron.,23, 4317 (1967).
F. Kállay, Recent Developments in the Chemistry of Natural Carbon Compounds.,5, 154 (1973).
A. E. Sammour and M. Elkasaby, J. Chem. U.A.R.,12, 1 (1969).
Mg. Joshi and K. N. Wadodkar, Indian J. Chem.,20B, 1089 (1981).
M. S. Paur, G. C. Rovnyak, A. I. Cohen, B. Toeplitz, J. Z. Gougoutas, J. Org. Chem.,44, 2513 (1979).
G. C. Rovnyak and V. Shu, J. Org. Chem.,44, 2518 (1979).
T. Loránd, D. Szabó, A. Földesi, L. Párkányi, A. Kálmán, and A. Neszmélyi, J. Chem. Soc., Perkin Trans. 1., 481 (1985).
W. I. Awad, M. F. Ismail, and A. H. Moustafa, U.A.R. J. Chem.,14, 561 (1971).
Ger. Offen. 2520171, C. F. Turk; Chem. Abs.,84, 74261 (1976).
U. S. Pat. 3,969,527; J. Krapcho and J. Schwartz; Chem. Abs.,85, 77415 (1976).
N. R. El-Rayyes and A. Al-Jawhary, J. Heterocycl. Chem.,23, 135 (1986).
N. R. El-Rayyes and N. H. Bahtiti, J. Heterocycl. Chem.,26, 209 (1989).
A. Szöllösy, G. Tóth, T. Loránd, T. Kónya, F. Aradi, and A. Lévai, J. Chem. Soc. Perkin Trans. II, 489 (1991).
H. M. Faidallah and M. S. I. Makki, J. Chinese Chem. Soc.,41, 585 (1994).
T. Loránd, F. Aradi, A. Szöllösy, C. Toth, and T. Kónya, Monatsh. Chem.,127, 971 (1996).
A. Lévai, A. Szöllösy, and G. Tóth, J. Chem. Res. (S)., 392 (1985).
A. Lévai, G. Tóth, and A. Szöllösy, Stud. Org. Chem. (Amsterdam),23, 47 (1986).
N. K. Sangwan and S. N. Rastogi, Indian J. Chem.,20B, 135 (1981).
N. K. Sangwan, J. Chem. Res. (S), 22 (1987).
G. Tóth, A. Szöllösy, T. Loránd, T. Kónya, D. Szabó, A. Földesi, and A. Lévai, J. Chem. Soc. Perkin Trans. II, 319 (1989).
Additional information
Department of Organic Chemistry, Kossuth Lajos University, Egyetem ter I, H 4010 Debrecen, Hungary. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 747–759, June, 1997.
Rights and permissions
About this article
Cite this article
Lévai, A. Synthesis of pyrazolines by the reactions ofα,β-enones with diazomethane and hydrazines (review). Chem Heterocycl Compd 33, 647–659 (1997). https://doi.org/10.1007/BF02291794
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02291794