Abstract
The cyclization of N-alkylquinoxalinium salts with the anions of β-dicarbonyl compounds proceeds regioselectively and stereoselectively and leads to endo-3a, 4,9,9a-tetrahydrofuro[2,3-b]quinoxalines. The structure of the cycloadducts was established on the basis of the 1H and 13C NMR spectra and the results of x-ray diffraction analysis.
Similar content being viewed by others
Literature cited
V. N. Charushin, O. N. Chupakhin, and A. I. Rezvukhin, Heterocycles, 16, No. 2, 195 (1981).
M. J. Strauss, Acc. Chem. Res., 7, 181 (1974).
M. J. Strauss, T. C. Jensen, H. Schran, and K. O'Conner, J. Org. Chem., 35, 383 (1970).
R. R. Bard and M. J. Strauss, J. Am. Chem. Soc., 97, 3789 (1975).
R. R. Bard and M. J. Strauss, J. Org. Chem., 42, 2589 (1977).
D. C. Palmer and M. J. Strauss, Chem. Rev., 77, 1 (1977).
M. J. Strauss, D. C. Palmer, and R. R. Bard, J. Org. Chem., 43, 2041 (1978).
B. De Croix, M. J. Strauss, A. D. Fusco, and D. C. Palmer, J. Org. Chem., 44, 1700 (1979).
P. Barczynski and H. C. van der Plas, Rec. Trav. Chim., 97, 256 (1978).
E. Matsumura, M. Ariga, and Y. Tohda, Tetrahedron Lett., No. 16, 1393 (1979).
V. N. Charushin, I. Ya. Postovskii, and O. N. Chupakhin, Dokl. Akad. Nauk SSSR, 246 351 (1979).
O. N. Chupakhin, V. N. Charushin, and Yu. V. Shnurov, Zh. Org. Khim., 16, 1064 (1980).
J. W. Bunting and M. G. Meathrel, Can. J. Chem., 50, 919 (1972).
Yu. Yu. Popelis, É. É. Liepin'sh, and Ya. P. Stradyn', Khim. Geterotsikl. Soedin., No. 2, 167 (1980).
G. G. Melikyan, D. A. Mkrtchyan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 7, 884 (1980).
D. Gagnaire and E. Payo-Subiza, Bull. Soc. Chim. Fr., No. 12, 2633 (1963).
T. Yanami, A. Ballatore, M. Miyashita, M. Kato, and A. Yoshikoshi, J. Chem. Soc., Perkin Trans. I, No. 10, 1144 (1978).
J. L. Marshall and R. Walter, J. Am. Chem. Soc., 96, 6358 (1974).
R. M. Wilson, E. J. Gardner, R. C. Elder, R. H. Squire, and L. K. Florian, J. Am. Chem. Soc., 96, 2955 (1974).
L. Yu. Ukhin, V. V. Bessonov, A. I. Yanovskii, T. V. Timofeeva, N. G. Furmanova, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., No. 4, 461 (1980).
T. Gilchrist and R. C. Storr, Organic Reactions and Orbital Symmetry, Cambridge University Press (1972).
S. J. Yan, W. H. Burton, P. L. Chien, and C. C. Cheng, J. Heterocycl. Chem., 15, 297 (1978).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 2.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1392–1398, October, 1981.
Rights and permissions
About this article
Cite this article
Chupakhin, O.N., Charushin, V.N., Klyuev, N.A. et al. Cyclization of N-alkylazinium cations with bisnucleophiles. 3. endo adducts in the reaction of quinoxalium salts with β-diketones and their x-ray diffraction analysis. Chem Heterocycl Compd 17, 1046–1052 (1981). https://doi.org/10.1007/BF00503539
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00503539