Abstract
The products of the addition of diazomethane to the double bond of α-, β-, and γ-vinyl-pyridines, 2-propenyl-, 2-styryl-, and 2-(p-nitrostyryl)pyridines, and β-(2-pyridyl)acrylic acid were obtained. When a hydrogen atom or alkyl or phenyl group is present in the β-position of the vinyl group, 3-pyridyl-Δ2-pyrazolines are formed (they are isolated as the acetyl derivatives). Electron-acceptor substituents (COOCH3 and C6H4NO2) in this position disrupt the polarization, and this leads to the formation of a mixture of two isomeric pyrazolines. The primary formation of Δ1-pyrazolines was proved by means of IR and UV spectroscopy.
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Literature cited
P. B. Terent'ev, A. N. Kost, M. Islam, and I. V. Chaikovskii, Khim. Geterotsikl. Soedin., 1659 (1970).
S. Patai (editor), Chemistry of the Alenes, Wiley (1964).
R. Huisgen, Angew. Chem., 75, 604, 742 (1963).
S. D. Andrews, A. C. Day, and A. N. McDonald, J. Chem. Soc., C, 787 (1969).
A. Ledwith and D. Parry, J. Chem. Soc., C, 1408 (1966).
A. Ledwith and J. Shin-Zin, J. Chem. Soc., B, 83 (1967).
W. E. Parham, F. D. Blake, and D. R. Theissen, J. Org. Chem., 27, 2415 (1962).
A. A. Artamonov, B. A. Rozenberg, and A. K. Sheinkman, in: Reactions and Methods of Investigation of Organic Compounds [in Russian], Vol. 14, Khimiya, Leningrad (1964), p. 173.
A. N. Kost, P. B. Terent'ev, and M. A. Chernova, Vestnik MGU, Ser. Khim., No. 2, 59 (1964).
J. M. Steward, R. L. Clark, and P. E. Pike, J. Chem. Eng. Data, 16, 98 (1971).
R. J. Crawfold, A. Mishra, and R. J. Dumniel, J. Am. Chem. Soc., 88, 3959 (1966).
P. Grammaticakis, Bull. Soc. Chim. France, 690 (1950).
L. A. Walter, W. H. Hunt, and R. J. Fostinder, J. Am. Chem. Soc., 63 2771 (1941).
A. W. Jonson, J. Org. Chem., 25, 2237 (1960).
B. D. Shaw and E. A. Wagstaff, J. Chem. Soc., 77 (1933).
W. Reid and H. Keller, Ber., 89, 2578 (1956).
Organic Synthesis [Russian translation], Vol. 2, Inostr. Lit., Moscow (1949), p. 373.
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See [1] for communication IX.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 64–69, January, 1973.
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Terent'ev, P.B., Vinogradova, S.M., Kost, A.N. et al. Properties of a multiple bond conjugated with the pyridine ring. Chem Heterocycl Compd 9, 55–59 (1973). https://doi.org/10.1007/BF00476150
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DOI: https://doi.org/10.1007/BF00476150