Abstract
Based on the previously developed program for computer prediction of recyclization (GREH) and analysis of literature data on ring opening in bridged azolopyridines, we propose specific types of substituted substrates capable of undergoing previously unknown classes of isomerization and recyclization. We discuss the criteria for expert assessment of the computer predictions and heuristic principles for design of the structures of such substrates (the empirical principle of the maximally alternant tree in the bicycle), increasing the probability of experimental observation of the predicted conversions.
Similar content being viewed by others
References
D. E. Lushnikov and E. V. Babaev, Khim. Geterotsikl. Soedin., No. 10, 1299 (1993).
E. V. Babaev, Khim. Geterotsikl. Soedin., No. 8, 1141 (1995).
E. V. Babaev, A. V. Efimov, and D. A. Maiboroda, Khim. Geterotsikl. Soedin., No. 8, 1104 (1995).
E. V. Babaev, V. N. Torochesnikov, and S. I. Bobrovskii, Khim. Geterotsikl. Soedin., No. 9, 1235 (1995).
D. A. Maiboroda and E. V. Babaev, Khim. Geterotsikl. Soedin., No. 11, 1445 (1995).
A. Kekulé, The Constitution of Pyridines [in German], Vol. 2, Verlag Chemie, Berlin (1929). p. 768.
H. C. van der Plas, Ring Transformation of Heterocycles, Vols. 1 and 2, Academic Press, London (1973). and 2.
E. V. Babaev, D. E. Lushnikov, and N. S. Zefirov, J. Am. Chem. Soc.,115, 2416 (1993).
E. V. Babaev and N. S. Zefirov, Bull. Soc. Chim. Belg.,101, 67 (1992).
E. V. Babaev and N. S. Zefirov, Khim. Geterotsikl. Soedin., No. 6, 808 (1992).
E. V. Babaev and N. S. Zefirov, J. Mathem. Chem., No. 11, 65 (1992).
N. S. Zefirov and S. S. Tratch, Chem. Scripta,15, 4 (1980).
N. S. Zefirov, Accts. Chem. Res.,20, 237 (1987).
N. S. Zefirov and S. S. Tratch, Anal. Chim. Acta,235, 115 (1990).
S. Fujita, J. Chem. Inf. Comp. Sci.,26, 205 (1986).
S. Fujita, J. Chem. Inf. Comp. Sci.,28, 128 (1988).
R. Herges, Tetrah. Comput. Methodology,1, No. 11, 15 (1988).
E. V. Babaev, Dissertation in competition for the academic degree of Candidate of the Chemical Sciences, Moscow State University, Moscow (1987).
S. I. Bobrovskii, E. V. Babaev, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 6, 758 (1990).
K. Valentin and A. Taurins, Tetrahedron Lett.,30, 3621 (1966).
W. W. Paudler, R. A. VanDahm, and Y. N. Park, J. Heterocycl. Chem.,9, 81 (1972).
A. Tschitschibabin, Ber.,59, 2048 (926).
Gy. Hajos and A. Messmer, J. Heterocycl. Chem.,23, 809 (1984).
Gy. Hajos, A. Messmer, and T. Koritsanszky, J. Org. Chem.,52, 2015 (1987).
A. Lawson and D. H. Miles, J. Chem. Soc., No. 3, 2865 (1959).
A. Lawson and D. H. Miles, J. Chem. Soc., No. 2, 1945 (1960).
H. Petride and D. Railenau, Rev. Roum. Chim.,33, 729 (1988).
H. Petride, Rev. Roum. Chim.,36, 1299 (1991).
G. V. Boyd and P. H. Wright, J. Chem. Soc. (C).,10, 1485 (1970).
C. K. Bradsher and M. Zinn, J. Heterocycl. Chem.,1, 219 (1964).
H. Pauls and F. Kroenke, Chem. Ber.,109, 3646 (1976).
C. K. Bradsher, R. D. Brandau, J. E. Boilek, and T. L. Hough, J. Org. Chem.,34, 2129 (1969).
A. R. Katritzky and A. Zia, J. Chem. Soc., Perkin Trans. 1,11, 131 (1982).
G. Markl and S. Pflaum, Tetrahedron Lett.,28, 1511 (1987).
K. Satoh T. Miyasaka, and K. Arakawa, Yakugaku Zasschi,97, 422 (1977); Chem. Abstr.,82:1022555 (1977) [sic].
E. V. Babaev, Ros. Khim. Zh. (Zh. Ros. Khim. O-va im D. I. Mendeleeva),38, 54 (1994).
E. V. Babaev, Khim. Geterotsikl. Soedin., No. 7, 937 (1993).
E. V. Babaev, AIP Conference Proceedings, Vol. 330 (ECCC 1. Comput. Chem., Nancy, France, May 1994), AIP Press, Woodbury NY (1995), p. 746.
J. W. Cornforth in: Heterocyclic Compounds, Vol. 5, R. C. Elderfield (ed.) [Russian translation], p. 242.
P. Molina, M. Alajarin, M. J. Perez de Vega, M. C. Foces-Foces, and C. F. Hernandez, Chem. Ber.,121, 1495 (1988).
S. I. Bobrovskii, E. V. Babaev, S. P. Gromov, K. A. Paseshnichenko, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 2, 209 (1987).
E. V. Babaev, S. V. Bozhenko, and A. V. Efimov, in: Abstracts, Twelfth Symposium on Chemistry of Heterocyclic Compounds, Brno, Sept. 1–4, 1996, p. 21.
E. V. Babaev, D. A. Maiboroda, A. V. Efimov, K. Yu. Pasichnichenko, and D. Yu. Migachev, Carbonyl Compounds in Synthesis of Heterocycles [in Russian], Saratov (1996), p. 200.
Additional information
Dedicated to É. Ya. Lukevits on his 60th birthday.
For communications 4 and 5, see [1, 2].
M. V. Lomonosov State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, Nos. 11–12, pp. 1564–1580, November–December, 1996. Original article submitted October 15, 1996.
Rights and permissions
About this article
Cite this article
Babaev, E.V., Zefirov, N.S. Molecular design of heterocycles. 6. Hetarenes with bridge nitrogen atom. 4. Strategy and tactics for computer prediction of new recyclizations in the azolopyridine series with bridge nitrogen atom. Chem Heterocycl Compd 32, 1344–1357 (1996). https://doi.org/10.1007/BF01169965
Issue Date:
DOI: https://doi.org/10.1007/BF01169965