Abstract
The geometry of dihydropyridine and its alkyl derivatives was studied by the molecular mechanics method. The dihydrocycle was found to be mobile; however, substituents exert little effect on its distorted sofa conformation. The alkyl groups attached to the saturated carbon atoms occupy pseudo-equatorial position in monosubstituted and pseudo-axial positions in disubstituted 3,4-dihydropyridines. Unusually high barriers to inversion of the dihydrocycle were observed incis-3,4-dialkyl-3,4-dihydropyridines caused by the eclipse of the substituents in the transition state.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J. Kuthan and A. Kurfurst,Ind. Eng. Chem., Prod. Res. Dev., 1982,21, 191.
A. Sausing and G. Duburs,Heterocycles, 1988,27, 269.
A. Sausing and G. Duburs,Heterocycles, 1988,27, 991.
M. Schwarz, P. Trska, and J. Kuthan,Coll. Czech. Chem. Commun., 1988,54, 1854.
L. Fuentes, J. J. Vaguero, J. C. del Castillo, M. I. Ardid, and J. L. Soto,Heterocycles, 1985,23, 93.
J. W. Streef, H. S. van der Plas, J. J. Wei, J. P. Delercq, and M. van Meerssche,Heterocycles, 1987,26, 685.
J. L. Balcazar, F. Florencio, and S. Garcia-Blanco,Z. Kristallogr., 1986,174, 247.
A. N. Vereshchanin,Usp. Khim., 1983,52, 1879 [Russ. Chem. Rev., 1983,52 (Engl. Transl.)].
H. Oberhammer and S. H. Bauer,J. Am. Chem. Soc., 1969,91, 10.
L. A. Carreira, R. O. Carter, and J. R. Durig,J. Chem. Phys., 1973,59, 812.
N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya,J. Phys. Org. Chem., 1990,3, 147.
J. T. Sprague, J. C. Tai, and N. L. Allinger,J. Comput. Chem., 1987,8, 581.
J. C. Tai and N. L. Allinger,J. Am. Chem. Soc., 1988,110, 2050.
O. V. Shishkin, T. V. Timofeeva, S. M. Desenko, V. D. Orlov, S. V. Lindeman, and Yu. T. Struchkov,Izv. Akad. Nauk, Ser. Khim., 1993, 1217 [Russ. Chem. Bull., 1993,42, 1160 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1009–1012, June, 1994.
Rights and permissions
About this article
Cite this article
Shishkin, O.V., Polyakova, A.S., Desenko, S.M. et al. Conformational analysis of 3,4-dihydropyridine and its alkyl derivatives. Russ Chem Bull 43, 944–947 (1994). https://doi.org/10.1007/BF01558053
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01558053