Abstract
Published data and the results of the authors' own research on methods for the production of unsaturated 1,5-diketones and halogen-substituted 2-pentene-1,5-diones and their use in the synthesis of difficulty obtainable pyrylium, 3,5-dichloropyrylium, and 3-chlorothiopyrylium salts, aroylfurans, 40-chloroaroylfurans, isoxazolines, pyrazolines, 3,5-dichloropyridines, 1,4-tetramethylenebispyridines, and others are summarized. Aspects of the structure of 2-pentene-1,5-diones and their 2,4-dichloro-substituted analogs and features of their heterocyclization are discussed in comparison with pentane-1,5-diones and their 2,4-dichloro-substituted derivatives.
Similar content being viewed by others
References
W. Dilthey, J. Prakt. Chem.,94, 53 (1916).
W. Dilthey and R. Taucher, Chem. Ber.,53, 252 (1920).
I. Berson, J. Am. Chem. Soc.,74, 358 (1952).
I. P. Griot, I. Royer, and I. Dreux, Tetrahedron Lett., No. 26, 2195 (1969).
A. I. Pyshchev, Thesis for Candidate of Chemical Sciences [in Russian], Rostov University, Rostov-on-Don (1977).
I. I. Basselier, Ann. Chim.,6, 1131 (1961).
G. Rio and V. Fellion, Tetrahedron Lett.,25, 1213 (1962).
G. W. Fischer and M. Herrmann, J. Prakt. Chem.,326 No. No. 2, 287 (1984).
J. Becher, I. P. Jacobsen, C. Stidsen, T. Zimmermann, and G. W. Fischer, Acta Chem. Scand.,B41, 391 (1987).
A. Williams, J. Am. Chem. Soc.,93 2733 (1971).
A. I. Pyshchev, N. V. Shibaeva, S. S. Goryachev, and L. L. Pyshcheva, The Chemistry of Dicarbonyl Compounds Fifth All-Union Conference Honor of the 100th Birthday of Academician of the Academy of Sciences of the Latvian SSR Gustav Vanag. Abstracts [in Russian], Riga (1981), p. 193.
A. I. Pyshchev (Pyshcev), uN. G. Bokii, and Yu. T. Struchkov, Tetrahedron,34, 2131 (1978)
Yu. A. Zhdanov, É. A Zvezdina, S. M. Statsenko, and A. N. Maksimova, Khim. Geterotsikl. Soedin., No. 2, 182 (1987).
G. W. Fischer, J. Prakt. Chem.,327, 529 (1985).
L. P. Olekhnovich, I. B. Orenshtein, N. G. Tregub, G. N. Dorofeenko, and V. I. Minkin, Zh. Org. Khim.,13, 1124 (1977).
V. Fellion, Compt. Rend.,252, 207 (1961).
V. Fellion, Compt. Rend.252, 2898 (1961).
M. Simaltry, H. Streelesha, and H. Knedija, Bull. Soc. Chim. France, No. 10, 3603 (1971).
P. F. Devitt, J. Chem. Soc., No. 1, 510 (1958).
C. A. Henrick, E. Ritchie, and W. C. Taylor, Aust. J. Chem.,20, 2441 1967.
M. V. Nekhoroshev, V. H. Panov A. A. Bul'ber, and Yu. Okhlobystin, Zh. Obshch. Khim.,50, 958 (1980).
V. B. Panov M. V. Nekhoroshev, and A. A. Bjkbwe O. Yu. Okhlobystin Dokl. Acad Nauk SSSR,243, 372 (1978).
Additional information
N. G. Chernyshevskii Saratov State University, Saratov, K. A. Fedin Saratov State Pedagogical Institute, Saratov. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1319, October, 1996. Original article submmited June 8, 1995
Rights and permissions
About this article
Cite this article
Kharchenko, V.G., Pchelintseva, N.V. Unsaturated 1,5-diketones and their halogen-substituted derivatives — Preparation and use in the synthesis of heterocycles. Chem Heterocycl Compd 32, 1113–1130 (1996). https://doi.org/10.1007/BF01169220
Issue Date:
DOI: https://doi.org/10.1007/BF01169220