Abstract
Vinylation of 2-hydroxyquinoxaline affords either 2-vinyloxyquinoxaline or 1-vinyl-2-quinoxalone depending on the reaction conditions. The reactions of 2-hydroxyquinoxaline with 3-phenylprop-2-ynonitrile or 4-hydroxyalk-2-ynonitriles yield 3-phenyl-3-(quinoxalyl-2-oxy)prop-2-enonitrile or 4-hydroxy-3-(quinoxalyl-2-oxy)alk-2-enonitriles, respectively.
Similar content being viewed by others
References
D. G. Kim and O. V. Pryakhina,Khim. Geterotsikl. Soedin., 1996, 1026 [Chem. Heterocycl. Compd., 1996 (Engl. Transl.)].
G. G. Skvortsova, S. M. Tyrina, and V. K. Voronov,Khim. Geterotsikl. Soedin. 1971, 798 [Chem. Heterocycl. Compd., 1971 (Engl. Transl.)].
Z. V. Stepanova, G. G. Skvortsova, M. A. Andriyankov, and D. G. Kim.Tez. dokl. II Simp. po khimii i tekhnologii geterotsiklicheskikh soedinenii goryuchikh iskopaemykh [Abstrs. of Papers, II Symp. Chemistry and Technology of Heterocyclic Compounds from Fossile Fuels], Donetsk. 1973, 40 (in Russian).
L. V. Andriyankova, A. G. Mal'kina, E. I. Kositsyna, L. N. Il'icheva, A. I. Albanov, and B. A. Trofimov,Zh. Org. Khim., 1999,35, 294 [Russ. J. Org. Chem., 1999,35 (Engl. Transl.)].
J. A. Joule and G. F. Smith,Heterocyclic Chemistry, Van Nostrand Reinhold, New York, 1972, 362 pp.
A. Albert and G. B. Barlin,J. Chem. Soc., 1962, 3129.
B. A. Trofimov,Geteroatomnye proizvodnye atsetilena [Heteroatomic Acetylene Derivatives], Nauka, Moscow, 1981, 206 pp. (in Russian).
K. Nakanishi,Infrared Absorption Spectroscopy, Holden-Day, Inc., San Francisco; Nancodo Company Ltd, Tokyo, 1962, 216 pp.
M. A. Andriyankov, A. V. Afonin, and M. V. Nikitin,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1176 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 1070 (Engl. Transl.)].
A. V. Afonin, A. V. Vashchenko, M. A. Andriyankov, V. K. Voronov, E. I. Enikeeva, and L. L. Dmitrieva,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1539 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1392 (Engl. Transl.)].
A. V. Afonin, A. V. Vashchenko, T. Takagi, and H. Fujiwara,Bull. Chem. Soc. Jpn., 1996,69, 933.
Chemistry of Acetylenes, Ed. H. G. Viehe, Marcel Dekker, New York, 1969.
R. N. Kudyakova, Yu. M. Skvortsov, A. G. Mal'kina, E. I. Kositsyna, and V. B. Modonov,Zh. Org. Khim., 1991,27, 521, [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].
Yu. M. Skvortsov, A. G. Mal'kina, E. Y. Moshchevitina, V. B. Modonov, and B. A. Trofimov,Sulfur Lett., 1989,9(4), 141.
S. R. Landor, B. Demetriou, R. Grzeskowiak, and D. Pavey,J. Organometal. Chem., 1975,93, 129.
Yu. M. Skvortsov, A. G. Mal'kina, A. N. Volkov, B. A. Trofimov, E. B. Oleinikova, I. V. Kazin, and V. V. Gedymin.Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 872 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978,27, 754 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 738–741, April, 2000.
Rights and permissions
About this article
Cite this article
Andriyankova, L.V., Zhiyet'ev, S.A., Andriyankov, M.A. et al. Nucleophilic addition of 2-hydroxyquinoxaline to acetylenes. Russ Chem Bull 49, 740–743 (2000). https://doi.org/10.1007/BF02495494
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02495494