Abstract
According to the 1H NMR, IR, and electronic absorption spectra and X-ray diffraction data, 2-aryl-1-benzoyl-1-nitroethenes have E configuration with predominant s-cis conformation, where the nitro group lies in the plane of the double carbon-carbon bond, while the carbonyl group deviates from that plane. Reactions of 2-aryl-1-benzoyl-1-nitroethenes with pyrrole and N-methylpyrrole gave the corresponding alkylation products at the C2 atom in the heteroring.
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Yanovskaya, L.A., Kryshtal’, G.V., and Kul’ganek, V.V., Usp. Khim., 1984, vol. 53, no. 8, p. 1280.
Orlov, V.D., Kolosov, M.A., Kotlyar, V.N., Marrugo Gonzalez, A.Kh., Sidorenko, D.Yu., Pushkarev, A.P., and Baraban, A.Yu., Sbornik nauchnykh trudov Vserossiiskoi nauchno-prakticheskoi konferentsii “Korshunovskie chteniya” (Collection of Scientific Papers Presented at the All-Russian Scientific and Practical Conf. “Korshunov’s Readings”), Tol’yatti, 2008, p. 11.
Shikhaliev, Kh.E., Falaleev, A.V., and Kryl’skii, D.V., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 450.
Desenko, S.M., Chebanov, V.A., Kolos, N.N., and Orlov, V.D., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 140.
Desenko, S.M. and Orlov, V.D., Azageterotsikly na osnove aromaticheskikh nepredel’nykh ketonov (Aza Heterocycles Based on Aromatic Unsaturated Ketones), Khar’kov: Folio, 1998.
Fel’gendler, A.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2000, vol. 70, no. 7, p. 1087.
Bakhareva, S.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2001, vol. 71, no. 9, p. 1493.
Aboskalova, N.I., Berestovitskaya, V.M., Bakhareva, S.V., and Fel’gendler, A.V., Khim. Geterotsikl. Soedin., 2002, no. 10, p. 1462.
Berestovitskaya, V.M., Aboskalova, N.I., Ishmaeva, E.A., Bakhareva, S.V., Berkova, G.A., Vereshchagina, Ya.A., Fel’gendler, A.V., and Fattakhova, G.R., Russ. J. Gen. Chem., 2001, vol. 71, no. 12, p. 1942.
Remennikov, G.A., Khim. Geterotsikl. Soedin., 1997, no. 12, p. 1587.
Paperno, T.Ya., Perekalin, V.V., and Sopova, A.S., Zh. Prikl. Spektrosk., 1973, vol. 19, no. 4, p. 649.
Savin, V.I. and Kitaev, Yu.P., Zh. Org. Khim., 1973, vol. 9, no. 6, p. 1101.
Bellamy, L.J., Advances in Infra-red Group Frequencies, London: Methuen, 1966. Translated under the title Novye dannye po IK spektram slozhnykh molekul, Moscow: Mir, 1971, p. 172.
He, L., Srikanth, G.S.C., and Castle, S.L., J. Org. Chem., 2005, vol. 70, no. 20, p. 8140.
Aboskalova, N.I., Smirnova, N.N., Kataeva, O.N., Baichurin, R.I., Fel’gendler, A.V., Berkova, G.A., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2008, vol. 78, no. 9, p. 1711.
Andrianov, V.G., Struchkov, Yu.T., and Babievsky, K.K., Cryst. Struct. Commun., 1982, vol. 11, p. 31.
Aboskalova, N.I., Berestovitskaya, V.M., Berkova, G.A., and Fel’gendler, A.V., Russ. J. Org. Chem., 1999, vol. 35, no. 1, p. 151.
Sheldrick, G.M., SHELXTL Ver.5.0. Software Reference Manual, Siemens Industrial Automation: Madison WI, 1995.
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Original Russian Text © V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova, K.A. Lysenko, G.A. Berkova, A.V. Fel’gendler, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1697–1702.
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Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I. et al. α-Nitro chalcones: Structure and reaction with pyrrole. Russ J Gen Chem 79, 2191–2196 (2009). https://doi.org/10.1134/S1070363209100181
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DOI: https://doi.org/10.1134/S1070363209100181