Conclusions
-
1.
Cyclic and acyclicα,β-unsaturated ketones and their vinylogs, containing not more than three double bonds, and also 2-acetyl-5-methylfuran and 2-acetyl-5-methylthiophene, are capable of condensing withβ-dimethylaminoacrolein acetal aminal and 1,1,3-trimethoxy-3-dimethylaminopropane not only at either theα-methyl or methylene group, but also at the CH3 group, separated from the carbonyl by either double bonds or a heterocycle.
-
2.
We synthesized and studied by physicochemical methods some acyclic polyenic bis-ω,ω′- and monocu-dimethylamino ketones, and also those containing a cyclohexane, thiophene, or furan ring in the polymethine chain.
Similar content being viewed by others
Literature cited
Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof'ev, V. A. Petukhov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 595.
Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof'ev, V. A. Petukhov, and V. F. Kucherov, Inventor's Certificate No. 479,758, Aug. 5, 1975; Byull. Izobr., No. 29 (1976).
Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof'ev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 116;1978, 392.
Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof'ev, and V. F. Kucherov, Inventor's Certificate No. 536,- 165, Nov. 25, 1976; Byull. Izobr., No. 43 (1977).
Zh. A. Krasnaya, E. P. Prokof'ev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 123.
I. N. Nazarov, I. I. Nazarova, and I. V. Torgov, Dokl. Akad. Nauk SSSR,122, 81 (1958).
T. Cuvigny and H. Normant, Bull. Soc. Chim. France.1960, 515.
M. W. Cronyn and C. H. Riesser, J. Am. Chem. Soc.,75, 1666 (1953).
L. A. Yanovskaya and G. V. Kryshtal, Usp. Khim.,14, 1646 (1976).
Houben-Weyl, Methoden der Organischen Chemie, Vol. 7, Part 1, Stuttgart (1954), p. 85.
Yu. M. Shapiro, Khim. Geterotsikl. Soedin.,1971, 1168.
E. P. Prokof'ev, Zh. A. Krasnaya, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1972, 2218.
Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof'ev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 2511.
E. P. Prokof'ev and Zh. A. Krasnaya, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 2301;1980, 1011.
E. P. Prokof'ev, Zh. A. Krasnaya, and K. M. Litvak, Izv. Akad. Nauk SSSR, Ser. Khim.,1979, 766.
S. S. Malhotra and M. C. Whiting, J. Chem. Soc.,1960, 3812.
H. Bredereck, F. Effenberger, R. Gleiter, and K. A. Hirch, Angew. Chem.,77, 1010 (1965).
H. Bredereck, F. Effenberger, D. Zeyfang, and K. A. Hirch, Chem. Ber.,101, 4046 (1968).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1362–1373, June, 1980.
Rights and permissions
About this article
Cite this article
Krasnaya, Z.A., Stytsenko, T.S., Prokof'ev, E.P. et al. Synthesis of polyenic bis-ω,ω′- and mono-ω-dimethylamino ketones. Russ Chem Bull 29, 980–986 (1980). https://doi.org/10.1007/BF00958821
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00958821