Abstract
The literature on the reactions of 2-pyridones and their thio analogs with unsaturated compounds taking place by a mechanism of diene synthesis or of substitutive addition, depending on the structure of the initial components, has been systematized. The basic synthetic directions of the use of these reactions and also the stereochemistry of the diene synthesis with 2-pyridones and 2-thiopyridones are considered.
Similar content being viewed by others
Literature cited
O. Diels and K. Alder, Ann. Chem., 1490, 257 (1931).
N. P. Shusherina, Usp. Khim., 43, 1771 (1974).
B. Thyagarjan and K. Rajagopalan, Tetrahedron, 19, 1483 (1963).
B. Thyagarjan, K. Rajagopalan, and P. Gopalakrishnan, J. Chem. Soc., B, No. 3, 300 (1968).
B. Weinstein and D. Brattesani, J. Org. Chem., 32, 4107 (1967).
L. Paquette, J. Org. Chem., 30, 2107 (1965).
R. Adams and A. Schrecker, J. Am. Chem. Soc., 71, 1186 (1949).
J. A. Elvidge and L. Jackman, J. Chem. Soc., No. 3, 859 (1961).
M. Cook and A. Katritzky, J. Chem. Soc., Perkin Trans. II, No. 9, 1295 (1972).
M. Cook and A. Katritzky, P. Linda, and R. Back, Chem. Commun., No. 10, 510 (1971).
L. Betaneli, Dissertation for the Degree Candidate of Chemical Sciences [in Russian], Moscow State University, Moscow (1974).
L. Bauer, C. Bell, and G. J. Wright, J. Heterocycl. Chem., 3, 393 (1966).
E. Sheinin, G. Wright, C. Bell, and L. Bauer, J. Heterocycl. Chem., 5, 859 (1968).
R. Acheson and R. Tasker, J. Chem. Soc., C, No. 16, 1542 (1967).
H. Tomisawa and H. Hongo, Tetrahedron Lett., No. 29, 2465 (1969).
H. Tomisawa and H. Hongo, Chem. Pharm. Bull., 18, 925 (1970).
N. P. Shusherina, L. V. Betaneli, and A. U. Stepanyants, Dokl. Akad. Nauk SSSR, 213, 115 (1973).
H. Tomisawa, R. Fujita, K. Noguchi, and H. Hongo, Chem. Pharm. Bull., 18, 941 (1970).
G. Gisby, S. Royall, and P. Sammes, J. Chem. Soc., Perkin Trans. I, No. 2, 169 (1982).
N. P. Shusherina and Mokhamed Said, Zh. Org. Khim., 12, 2270 (1976).
N. P. Shusherina, Mokhamed Said, and T. I. Likhanova, Zh. Org. Khim., 14, 841 (1978).
V. Kane, H. Werblood, and S. Levine, Heterocycl. Chem., 13, 673 (1976).
L. V. Betaneli, N. P. Shusherina, E. A. Tarkhanova, and A. U. Stepanyants, Zh. Org. Khim., 11, 417 (1975).
L. V. Betaneli, N. P. Shusherina, A. U. Stepanyants, and E. A. Tarkhanova, Zh. Org. Khim., 13, 1926 (1977).
P. Mariano, P. Huesmann, R. Beamer, and D. Dunaway-Mariano, Tetrahedron, 34, 2617 (1978).
N. P. Shusherina and V. S. Pilipenko, Zh. Org. Khim., 14, 895 (1978).
N. P. Shusherina and V. S. Pilipenko, Zh. Org. Khim., 15, 1277 (1979).
R. Gompper and A. Schmidt, Angew Chem., 92, 468 (1980).
N. P. Shusherina, V. S. Pilipenko, O. K. Kireeva, B. I. Geller, and A. U. Stepanyants, Zh. Org. Khim., 16, 2390 (1980).
V. S. Pilipenko and N. P. Shusherina, Zh. Org. Khim., 17, 2122 (1981).
M. Kornblum and G. Coffey, J. Org. Chem., 31, 3447 (1966).
N. P. Shusherina and L. V. Betaneli, Khim. Geterotsikl. Soedin., No. 9, 1247 (1974).
R. Adams and J. Pachter, J. Am. Chem. Soc., 74, 4906 (1952).
K. Undheim, Acta Chem. Scand., 23, 1715 (1969).
K. Undheim, Acta Chem. Scand., 27, 1749 (1973).
G. Ulsaker and K. Undheim, Acta Chem. Scand., 31B, 917 (1977).
I. Kh. Fel'dman and A. V. Voropaeva, Zh. Org. Khim., 34, 1547 (1964).
A. V. Voropaeva and Kh. Sh. Chibilyaev, Zh. Org. Khim., 34, 1548 (1964).
V. S. Pilipenko, Dissertation for the Degree Candidate of Chemical Sciences [in Russian], Moscow State University, Moscow (1980).
V. S. Pilipenko, F. A. Alimirzoev, and A. U. Stepanyants, Zh. Org. Khim., 15, 2586 (1979).
N. P. Shusherina and Mokhamed Said, Dokl. Akad. Nauk, 233, 606 (1974).
V. S. Pilipenko and N. P. Shusherina, Zh. Org. Khim., 16, 2444 (1980).
E. I. Fedorov, B. I. Mikhant'ev, and G. I. Khoroshavina, Khim. Geterotsikl. Soedin., No. 1, 215 (1967).
M. F. Shostakovskii, G. G. Skvortsova, S. M. Tyrina, Yu. L. Frolov, N. M. Deriglazov, V. V. Voronov, and N. A. Ivanova, Dokl. Akad. Nauk SSSR, 186, 620 (1969).
G. G. Skvortsova, D. G. Kum, and L. V. Andriyankova, Kh. Geterotsikl. Soedin., No. 3, 364 (1978).
N. P. Shusherina, O. V. Slavyanova, G. N. Rodionova, and R. Ya. Levina, Khim. Geterotsikl. Soedin., No. 4, 489 (1970).
U. Heep, Tetrahedron, 31, 77 (1975).
K. Undheim and L. Riege, J. Chem. Soc., Perkin Trans. I, No. 14, 1493 (1975).
S. A. Shevelev, Usp. Khim., 39, 1773 (1970).
G. Hopkins, J. Jonak, H. Minnemeyer, and H. L. Tieckelmann, J. Org. Chem., 32, 4040 (1967).
K. Somekawa, H. Hemura, T. Shimou, and S. Kumamoto, Nippon Kagaku Kaishi, 1071 (1979).
G. Gisby, S. Royall, and P. Sammes, Chem. Commun., No. 11, 501 (1979).
K. Matsumoto, Y. Ykemi-Kono, B. Uchida, and R. Acheson, Chem. Commun., No. 23, 1091 (1979).
N. P. Shusherina and M. V. Ganeeva, Zh. Org. Khim., 9, 848 (1973).
N. P. Shusherina, L. V. Betaneli, G. B. Mndlyan, and A. U. Stepanyants, Khim. Geterotsikl. Soedin., No. 11, 1512 (1974).
K. Somekawa, T. Watanabe, and S. Kumamoto, Nippon Kagaku Kaishi, 412 (1978); Chem. Abstr. 88, 190642 (1978).
N. P. Shusherina and L. V. Betaneli, Vestn. Mosk. Gos. Univ., Khim., 15, 496 (1974).
H. Tomisawa, H. Hongo, and R. Fujita, Symp. Heterocycl., p. 267 (1977); Chem. Abstr., 89, 146745 (1978).
H. Tomisawa, R. Fujita, K. Noguchi, and H. Hongo, Chem. Pharm. Bull., 20, 2328 (1978).
H. Tomisawa, H. Hongo, R. Fujita, and H. Kato, Heterocycles, 6, 1765 (1977).
H. Tomisawa, H. Hongo, R. Fujita, H. Kato, and A. Sato, Heterocycles, 8, 165 (1977).
H. Tomisawa, H. Hongo, J. Kato, R. Fujita, and A. Sato, Chem. Pharm. Bull., 28, 2312 (1978).
H. Tomisawa, H. Hongo, R. Fujita, H. Kato, and A. Sato, Heterocycles, 9, 107 (1978).
H. Tomisawa, H. Kato, T. Naraki, and R. Fujita, Chem. Pharm. Bull., 27, 392 (1979).
H. Hongo, Chem. Pharm. Bull., 20, 226 (1972).
H. Tomisawa, H. Kato, R. Fujita, and T. Naraki, Chem. Pharm. Bull., 27, 670; Chem. Abstr., 91, 56773 (1979).
H. Kato, R. Fujita, H. Hongo, and H. Tomisawa, Heterocycles, 12, 1 (1979).
H. Tomisawa, H. Kato, R. Fujita, and H. Hongo, Chem. Pharm. Bull., 27, 810 (1979).
J. Sauer, Angew. Chem., Engl. Ed., 6, 16 (1967).
N. Sh. Padyukova and V. L. Florent'ev, Khim. Geterotsikl. Soedin., No. 5, 600 (1973).
M. Lee and W. Herndon, J. Org. Chem., 43, 518 (1978).
K. Alder and G. Stein, Angew. Chem., 50, 510 (1937).
Y. Kobuke, T. Sugimoto, and J. Turukawa, J. Am. Chem. Soc., 94, 3633 (1970).
Y. Kobuke, T. Fueno, and J. Turukawa, J. Am. Chem. Soc., 92, 6548 (1970).
M. Kakushima, Can. J. Chem., 57, 2564 (1979).
Yu. Raifel'd, B. S. Él'yanov, and S. M. Makin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1090 (1976).
D. Eckroth, J. Org. Chem., 41, 394 (1976).
J. Meller and C. Webb, J. Chem. Soc., Perkin Trans. II, No. 1, 26 (1974).
H. Martin, R. Iden, and H. Schiwek, Tetrahedron Lett., 36, 3337 (1978).
L. Kalo and D. Ginsburg, Tetrahedron, 34, 2155 (1978).
J. Berson, R. Reynolds, and W. Jones, J. Am. Chem. Soc., 78, 6049 (1956).
A. S. Onishchenko, The Diene Synthesis [in Russian], Izd. Akad. Nauk SSSR (1963).
N. P. Shusherina, L. V. Betaneli, and A. B. Mndlyan, Vestn. Mosk. Gos. Univ., Khimiya, 17, 91 (1976).
P. Shusherina, M. T. Khakimi, A. U. Stepanyants, and I. V. Zlokazova, Zh. Org. Khim., 13, 854 (1977).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–20, January, 1984.
Rights and permissions
About this article
Cite this article
Shusherina, N.P., Pilipenko, V.S. The diene synthesis reaction and substitutive addition with 2-pyridones and their thio analogs (review). Chem Heterocycl Compd 20, 1–16 (1984). https://doi.org/10.1007/BF00505839
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00505839