Abstract
The reaction of 2-thiophene aldehyde, 2-acetylthiophene, 2-thiophene carboxylic acid, and its methyl ester with N-(hydroxymethyl)chloroacetamide in concentrated sulfuric acid yields a mixture of 4- and 5-(N-chloroacetylamino) methyl derivatives, the former being preferred.
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L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 4, 472 (1980).
R. O'Cinneide, Proc. Roy. Irish Acad., Sect. B,42, 359 (1935); Chem. Abs.,29, 7326 (1935).
H. D. Hartough, Thiophene and Its Derivatives, Interscience, New York (1952), pp. 253, 413.
H. E. Zaugg and W. B. Martin, “α-Amidoalkylations at Carbon,” in: R. Adams, ed., Organic Reactions, Vol. 14, Wiley, New York (1965), p. 56.
Ja. L. Gol'dfarb, Ju. B. Volkenstein, and L. I. Belen'kii, Angew. Chem.,80, 547 (1968).
L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 344 (1975).
Ya. L. Gol'dfarb, E. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim. No. 6, 1233 (1971).
L. I. Belen'kii, É. I. Novikova, I. A. D'yachenko, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 1736 (1971).
Ya. L. Gol'dfarb, É. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2841 (1971).
L. I. Belen'kii, É. I. Novikova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 10, 1353 (1971).
L. I. Belen'kii, I. B. Karmanova, É. I. Novikova, G. P. Gromova, Ya. L. Gol'dfarb, V. S. Bogdanov, and L. V. Shmelev, Zh. Org. Khim.,9, 1499 (1973).
Ya. L. Gol'dfarb, G. P. Gromova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2275 (1974).
A. P. Yakubov, L. I. Belen'kii, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 525 (1971).
R. V. Golovnya, A. L. Samusenko, and E. A. Mistryukov, J. High Resolution Chromatog. Chromatogr. Commun.,2, 609 (1979).
A. Einhorn and T. Mauermayer,: Ann.343, 282 (1905).
Ya. L. Gol'dfarb, A. P. Yakubov, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR,185, 94 (1969).
M. Pianka and D. J. Polton, British Patent 917, 924; Chem. Abs.,59, 1488 (1963).
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For Communication 25, see [1].
Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 793–797, June, 1986.
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Gol'dfarb, Y.L., Yakubov, A.P. & Belen'kii, L.I. Reactions of aromatic and heteroaromatic compounds carrying electron-acceptor substituents. 26. Acylaminomethylation of 2-acylthiophenes, 2-thiophenecarboxylic acid, and its esters. Chem Heterocycl Compd 22, 625–629 (1986). https://doi.org/10.1007/BF00575243
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DOI: https://doi.org/10.1007/BF00575243