Abstract
A series of 2-(indol-3-yl)-1-nitroethenes containing an ester, acetyl, benzoyl, or cyano group in the geminal position with respect to the nitro group have been synthesized, and their structure has been studied by 1H, 13C−{1H} NMR, IR, and UV spectroscopy.
Similar content being viewed by others
References
Perekalin, V.V., Sopova, A.S., and Lipina, E.S., Nepredel’nye nitrosoedineniya (Unsaturated Nitro Compounds), Leningrad: Khimiya, 1982.
Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjugated Nitrocompounds, Chichester: Wiley, 1994.
Karakhanov, R.A., Kelarev, V.I., and Polivin, Yu.N., Russ. Chem. Rev., 1993, vol. 62, no. 2, p. 169. doi https://doi.org/10.1070/RC1993v062n02ABEH000011
Berestovitskaya, V.M., Baichurin, R.I., and Aboskalova, N.I., Sopryazhennye nitroeteny, geminal’no aktivirovannye slozhnoefirnoi, tsiano- i atsil’noi gruppami (Conjugated Nitroethenes Geminally Activated by Ester, Cyano, and Acyl Groups), St. Petersburg: Asterion, 2014.
Izbrannye metody sinteza i modifikatsii geterotsiklov. Khimiya sinteticheskikh indol’nykh sistem (Selected Methods of Synthesis and Modification of Heterocycles. Chemistry of Sunthetic Indole Systems), Kartsev, V.G., Ed., Moscow: IBS, 2004, vol. 3.
Shul’ts, E.E., Kartsev, V.G., and Tolstikov, G.A., Khimiya i biologicheskaya aktivnost’ indol’nykh alkaloidov (Chemistry and Biological Activity of Indole Alkaloids), Moscow: ICSPF, 2018.
Sharma, V., Kumar, P., and Pathak, D., J. Heterocycl. Chem., 2010, vol. 47, no. 3, p. 491. doi https://doi.org/10.1002/jhet.349
Kaushik, N.K., Kaushik, N., Attri, P., Kumar, N., Kim, C.H., Verma, A.K., and Choi, E.H., Molecules, 2013, vol. 18, no. 6, p. 6620. doi https://doi.org/10.3390/molecules18066620
Singh, T.P. and Singh, O.M., Mini Rev. Med. Chem., 2018, vol. 18, no. 1, p. 9. doi https://doi.org/10.2174/1389557517666170807123201
Mal’tsev, O.V., Beletskaya, I.P., and Zlotin, S.G., Russ. Chem. Rev., 2011, vol. 80, no. 11, p. 1067. doi RC2011v080n11ABEH004249
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2012, 16th ed.
Zhungietu, G.I., Budylin, V.A., and Kost, A.N., Preparativnaya khimiya indola (Preparative Indole Chemistry), Kishinev: Shtiintsa, 1975
Baron, M., Metay, E., Lemaire, M., and Popowycz, F., J.Org. Chem., 2012, vol. 77, no. 7, p. 3598. doi https://doi.org/10.1021/jo2026096
Aksenov, A.V., Aksenov, N.A., Skomorokhov, A.A., Aksenova, I.V., Gryaznov, G.D., Voskressensky, L.G., and Rubin, M.A., Chem. Heterocycl. Compd., 2016, vol. 52, no. 11, p 923. doi https://doi.org/10.1007/s10593-017-1988-x
Abdelwaly, A., Salama, I., Gomaa, M.S., and Helal, M.A., Med. Chem. Res., 2017, vol. 26, no. 12, p. 3173. doi https://doi.org/10.1007/s00044-017-2011-x
Wang, Y.-C., Wang, J.-L., Burgess, K.S., Zhang, J.-W., Zheng, Q.-M., Pu, Y.-D., Yan, L.-J., and Chen, X.-B., RSC Adv., 2018, vol. 8, no. 11, p. 5702. doi https://doi.org/10.1039/c7ra13207g
Zhmurov, P.A., Ushakov, P.Yu., Novikov, R.A., Sukhorukov, A.Yu., and Ioffe, S.L., Synlett, 2018, vol. 29, no. 14, p. 1871. doi https://doi.org/10.1055/s-0037-1610213
Dornow, A. and Menzel, H., Justus Liebigs Ann. Chem., 1954, vol. 588, no. 1, p. 40. doi https://doi.org/10.1002/jlac.19545880105
Aboskalova, N.I., Cand. Sci. (Chem.) Dissertation, Leningrad, 1971.
Aboskalova, N.I., Polyanskaya, A.S., and Perekalin, V.V., Dokl. Chem., 1967, vol. 176, no. 4, p. 861.
Vinograd, L.Kh. and Suvorov, N.N., Chem. Heterocycl. Compd., 1970, vol. 6, no. 11, p. 1403. doi https://doi.org/10.1007/BF00476782
Umezawa, S. and Zen, S., Bull. Chem. Soc. Jpn., 1963, vol. 36, no. 9, p. 1150. doi https://doi.org/10.1246/bcsj.36.1150
Baranov, M.S. and Yampolsky, I.V., Tetrahedron Lett., 2013, vol. 54, no. 7, p. 628. doi https://doi.org/10.1016/j.tetlet.2012.11.132
Dornow, A. and Sassenberg, W., Justus Liebigs Ann. Chem., 1957, vol. 602, no. 1, p. 14. doi https://doi.org/10.1002/jlac.19576020102
Zalukaev, L.P., Sintez i reaktsii al’fa-nitroketonov (Synthesis and Reactions of α-Nitro Ketones), Riga: Akad. Nauk Latv. SSR, 1958.
Babievskii, K.K., Doctoral (Chem.) Dissertation, Moscow, 1980.
Kochetkov, K.A., Babievskii, K.K., Belikov, V.M., Garbalinskaya, N.S., and Bakhmutov, V.I., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, vol. 29, no. 3, p. 458. doi https://doi.org/10.1007/BF00949634
Lehnert, W., Tetrahedron, 1972, vol. 28, no. 3, p. 663. doi https://doi.org/10.1016/0040-4020(72)84029-8
Rodríguez, R., Viñets, I., Diez, A., Rubiralta, M., and Giralt, E., Synth. Commun., 1996, vol. 26, no. 16, p. 3029. doi https://doi.org/10.1080/00397919608004608
Rodríguez, R., Diez, A., Rubiralta, M., and Giralt, E., Heterocycles, 1996, vol. 43, no. 3, p. 513. doi https://doi.org/10.3987/COM-95-7327
Aboskalova, N.I., Polyanskaya, A.S., Perekalin, V.V., Demireva, Z.I., and Sokolova, L.N., J. Org. Chem. USSR, 1972, vol. 8, no. 6, p. 1349.
Polyanskaya, A.S., Perekalin, V.V., Aboskalova, N.I., and Sokolova, L.N., USSR Inventor’s Certificate no. 335246; Byull. Izobret., 1972, no. 13.
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., Cand. Sci. (Chem.) Dissertation, St. Petersburg, 2001.
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. doi https://doi.org/10.1023/A:1014200612456
Baichurina, L.V., Baichurin, R.I., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2010, vol. 80, no. 10, p. 2022. doi https://doi.org/10.1134/S1070363210100221
Velezheva, V.S., Erofeev, Yu.V., and Suvorov, N.N., J. Org. Chem. USSR, 1980, vol. 16, no. 10, p. 1839.
Baichurin, R.I., Baichurina, L.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2013, vol. 83, no. 9, p. 1764. doi https://doi.org/10.1134/S1070363213090223
Baichurin, R.I., Aboskalova, N.I., Trukhin, E.V., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2015, vol. 85, no. 8, p. 1845. doi https://doi.org/10.1134/S1070363215080101
Wolinski, P., Jasiñski, R., Czamopismo Techniczne/Tech. Trans., 2018, vol. 2, p. 109. doi https://doi.org/10.4467/2353737XCT.18.024.7997
Polyanskaya, A.S., Perekalin, V.V., Aboskalova, N.I., Demireva, Z.I., Sokolova, L.N., and Abdulkina, Z.A., J. Org. Chem. USSR, 1979, vol. 15, no. 10, p. 859.
Shadrin, V.Yu., Cand. Sci. (Chem.) Dissertation, Leningrad, 1987.
Garming, A., Redwan, D., Gelbke, P., Kern, D., and Dierkes, U., Justus Liebigs Ann. Chem., 1975, no. 10, p. 1744. doi https://doi.org/10.1002/jlac.197519751003
Ried, W. and Köhler, E., Justus Liebigs Ann. Chem., 1956, vol. 598, no. 2, p. 145. doi https://doi.org/10.1002/jlac.19565980207
Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I., Baichurina, L.V., Trukhin, E.V., Fel’gendler, A.V., and Gensirovskaya, M.A., Russ. J. Gen. Chem., 2016, vol. 86, no. 6, p. 1266. doi https://doi.org/10.1134/S1070363216060086
Berestovitskaya, V.M., Ishmaeva, E.A., Litvinov, I.A., Vasil’eva, O.S., Vereshchagina, Ya.A., Ostroglyadov, E.S., Fattakhova, G.R., Beskrovnyi, D.V., and Aleksandrova, S.M., Russ. J. Gen. Chem., 2004, vol. 74, no. 7, p. 1108. doi https://doi.org/10.1023/B:RUGC.0000045874.46434.ea
Bulatova, N.N. and Suvorov, N.N., Chem. Heterocycl. Compd., 1969, vol. 5, no. 5, p. 602. doi https://doi.org/10.1007/BF00957368
Young, E.H.P., J. Chem. Soc., 1958, no. 10, p. 3493. doi https://doi.org/10.1039/JR9580003493
Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR-spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.
Troschütz, R. and Grün, L., Archiv Pharm., 1993, vol. 326, no. 11, p. 857. doi https://doi.org/10.1002/ardp.19933261104
Babievskii, K.K., Bakhmutov, V.I., Kochetkov, K.A., Burmistrov, V.A., and Belikov, V.M., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, vol. 26, no. 2, p. 384. doi https://doi.org/10.1007/BF00921860
Aboskalova, N.I., Babievskii, K.K., Belikov, V.M., Perekalin, V.V., and Polyanskaya, A.S., J. Org. Chem. USSR, 1973, vol. 9, no. 5, p. 1082.
Author information
Authors and Affiliations
Corresponding author
Additional information
Russian Text © The Authors(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 5, pp. 671–683.
Supporting Information
Rights and permissions
About this article
Cite this article
Baichurin, R.I., Fedorushchenko, A.A., Aboskalova, N.I. et al. Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series. Russ J Gen Chem 89, 870–880 (2019). https://doi.org/10.1134/S1070363219050037
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363219050037