Abstract
Methyl and ethyl 2-(2-oxo-2,3-dihydro-3H-indol-3-ylidene)acetates react with aromatic amines to give products of regioselective addition at the α-position of the activated exocyclic C=C bond, methyl and ethyl 2-arylamino-2-(2-oxo-2,3-dihydro-1H-indol-3-yl)acetates.
Similar content being viewed by others
References
Roth, H.J. and Lausen, H.H., Arch. Pharm., 1973, vol. 306, p. 767; Chem. Abstr., 1974, vol. 80, no. 27049m.
Bajpai, S.N., Jain, R., and Joshi, K.C., Indian J. Chem., Sect. B, 1997, vol. 36, p. 1005; Chem. Abstr., 1998, vol. 128, no. 294763z.
Mogilaiah, K. and Rao, R.B., Indian J. Chem., Sect. B, 1998, vol. 37, p. 139; Ref. Zh., Khim., 1999, no. 14Zh223.
Kavali, J.R. and Badami, B.V., J. Chem. Res., Synop., 2000, p. 546; Ref. Zh., Khim., 2001, no. 01.13-19Zh318.
Dandia, A., Upreti, M., Rani, B., and Pant, U.C., J. Chem. Res., Synop., 1998, p. 752; Chem. Abstr., 1999, vol. 130, no. 153647u.
Dandia, A., Upreti, M., Rani, B., Pant, U.C., and Gupta, I.J., J. Fluorine Chem., 1998, vol. 91, p. 171; Chem. Abstr., 1999, vol. 130, no. 66476u.
Zhungietu, G.I., Dragalina, G.A., and Dorofeenko, G.N., Khim. Geterotsikl. Soedin., 1973, p. 40.
Otomasu, H., Tanaka, T., and Aoyagi, M., Chem. Pharm. Bull., 1976, vol. 24, p. 782; Chem. Abstr., 1976, vol. 85, no. 46497a.
Hassan, K.M. and Khalil, Z.H., J. Prakt. Chem., 1979, vol. 321, p. 870; Chem. Abstr., 1980, vol. 92, no. 163921q.
Joshi, K.C., Dandia, A., and Bhagat, S., Indian J. Chem., Sect. A, 1992, vol. 31, p. 98; Ref. Zh., Khim., 1993, no. 12Zh398.
El-Ahl, A.-A.S., Afeefy, H., and Metwally, M.A., J. Chem. Res., Synop., 1994, p. 14; Ref. Zh., Khim., 1994, no. 14Zh126.
Al-Thebeiti, M.S., Heteroatom Chem., 1994, vol. 5, p. 571; Chem. Abstr., 1995, vol. 123, no. 55734f.
Berezin, A.N., Koz’minykh, E.N., and Koz’minykh, V.O., Abstracts of Papers, V Molodezhnaya nauchnaya shkola-konferentsiya po organicheskoi khimii (Vth Youth Scientific School-Conf. on Organic Chemistry), Yekaterinburg: Ural. Otd. Ross. Akad. Nauk, 2002, p. 89.
Lomidze, K.Sh., Koz’minykh, E.N., Berezin, A.N., and Koz’minykh V.O., Materialy VIII Regional’noi nauchno-tekhnicheskoy konferentsii “Vuzovskaya nauka-Severo-Kavkazskomu regionu” (Proc. VIIIth Regional Conf. “High School Science for North Caucasian Region”), Stavropol’: Sev.-Kav. Gos. Tech. Univ., 2004, vol. 1, p. 26.
Koz’minykh, E.N., Berezin, A.N., Lomidze, K.Sh., and Koz’minykh, V.O., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2004, vol. 3, p. 535.
Koz’minykh, E.N., Igidov, N.M., Koz’minykh, V.O., Shavkunova, G.A., and Sof’ina, O.A., Russ. J. Org. Chem., 2000, vol. 36, p. 1341.
Koz’minykh, E.N., Doctoral (Pharm.) Dissertation, Perm’, 1999.
Koz’minykh, E.N., Berezina, E.S., and Koz’minykh, V.O., Russ. J. Gen. Chem., 1996, vol. 66, p. 1100.
Koz’minykh, E.N., Berezina, E.S., Kolla, V.E., Shelenkova, S.A., Voronina, E.V., and Koz’minykh, V.O., Khim.-Farm. Zh., 1997, vol. 31, no. 2, p. 31.
Osman, F.H. and El-Samahy, F.A., Phosphorus, Sulfur, Silicon Relat. Elem., 1998, vols. 134–135, p. 437; Ref. Zh., Khim., 1999, no. 11Zh274.
Author information
Authors and Affiliations
Additional information
Original Russian Text © V.O. Koz’minykh, V.I. Goncharov, A.V. Aksenov, E.N. Koz’minykh, K.Sh. Lomidze, A.N. Berezin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1373–1376.
Rights and permissions
About this article
Cite this article
Koz’minykh, V.O., Goncharov, V.I., Aksenov, A.V. et al. Regioselective addition of aromatic amines at the exocyclic C=C bond of 2-(2-Oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters. Russ J Org Chem 42, 1356–1359 (2006). https://doi.org/10.1134/S107042800609017X
Received:
Issue Date:
DOI: https://doi.org/10.1134/S107042800609017X