Abstract
X-ray structural data has shown that condensation of sym-3-nitrocollidine with benzaldehyde occurs at the 6-methyl group. The presence of an acceptor group in the side chain of 2,6-dimethyl-4-cyanomethyl-3-nitropyridine causes condensation to occur at the activated methylene group in the 4-position.
Similar content being viewed by others
References
N. N. Zatsepina and I. F. Typitsyn, Khim. Geterotsikl. Soedin., No. 12, 1587 (1974).
W. J. Spillone, P. Kavanagah, and F. Young, J. Chem. Soc. Perkin Trans. I, No. 6, 1763 (1981).
L. Achremovicz and Z. Skrowaczewska, Roczn. Chem.,39, 1417 (1965).
L. Achremovicz and Z. Skrowaczewska, Roczn. Chem.,41, 1555 (1967).
T. Bonas and Z. Skrowaczewska, Roczn. Chem.,43, 739 (1969).
F. Kogl, C. M. van der Want, and C. A. Salemnik, Rec. Trav. Chim.,67, 29 (1948).
M. Makosza, Synthesis, No. 2, 103 (1991).
M. Makosza, J. Golinski, and J. Baran, J. Org. Chem.,49, 1488 (1984).
A. Bondi, J. Phys. Chem.,170, 3006 (1966).
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. II, 1 (1987).
W. Robinson and G. M. Sheldick, Crystallographic Computing Techniques and New Technologies, Oxford Univ. Press, Oxford (1988), p. 366.
Additional information
M. V. Lomonosov State University, Moscow 119899. A. N. Nesmeyanov Institute of Organoelemental Compounds, Moscow 117813. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11. pp. 1543–1550, November, 1995. Original article submitted June 10, 1995.
Rights and permissions
About this article
Cite this article
Yurovskaya, M.A., Khamlova, I.G., Nesterov, V.N. et al. Regioorientation in the reaction of side chain activated alkylpyridines with electrophiles. Chem Heterocycl Compd 31, 1339–1345 (1995). https://doi.org/10.1007/BF01168629
Issue Date:
DOI: https://doi.org/10.1007/BF01168629