Abstract
A study was carried out on the reaction of pyrrolo[1,2-a]pyrazines containing an alkyl, aryl, or aralkyl substituent at C-1 with trifluoroacetic anhydride. Trifluoroacetylation products may be formed either by reaction in the pyrrole ring or at the aryl or aralkyl groups at C-1. Products of electrophilic substitution at C-6 are formed in the trifluoroacetylation of pyrrolo[1,2-a]pyrazines containing at C-1 a substituent bulkier than a methyl group but lacking substituents at C-6 (the α-position of the pyrrole ring).
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References
R. Buchan, M. Fraser, and P. Kong Thoo Lin, J. Org. Chem., 54, 1074 (1989).
J. M. Minguez, M. I. Castellote, J. J. Vaquero, J. L. Garcia-Navio, J. Alvarez-Builla, and O. Castaño, J. Org. Chem., 61, 4655 (1996).
W. Paudler and D. Dunham, J. Heterocycl. Chem., 2, 410 (1965).
G. Maury, Chem. Heterocycl. Comp., 30, 223 (1977).
W. Cooper, J. Org. Chem., 23, 1382 (1958).
V. I. Terenin, E. L. Ruchkina, K. V. Karapetyan, V. M. Mamaev, and Yu. G. Bundel, Khim. Geterotsikl. Soedin., 1566 (1995). [Chem. Heterocycl. Comp., 31, 1360 (1995)].
V. I. Terenin, E. V. Kabanova, N. A. Tselishcheva, M. A. Kovalkina, A. P. Pleshkova, and N. V. Zyk, Khim. Geterotsikl. Soedin., 431 (2004). [Chem. Heterocycl. Comp., 40, 351 (2004)].
M. Kawase, M. Teshima, S. Saito, and S. Tani, Heterocycles, 48, 2103 (1998).
S. I. Bobrovskii, D. E. Lushnikov, and Yu. G. Bundel, Khim. Geterotsikl. Soedin., 1634 (1989). [Chem. Heterocycl. Comp., 25, 1360 (1989)].
V. I. Terenin, E. V. Kabanova, and Yu. G. Bundel, Khim. Geterotsikl. Soedin., 763 (1991). [Chem. Heterocycl. Comp., 27, 597 (1991)].
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1226–1233, August, 2007.
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Terenin, V.I., Kabanova, E.V., Tselishcheva, N.A. et al. Trifluoroacetylation of pyrrolo[1,2-a]pyrazines. Chem Heterocycl Comp 43, 1038–1043 (2007). https://doi.org/10.1007/s10593-007-0162-2
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DOI: https://doi.org/10.1007/s10593-007-0162-2