Abstract
The review systemizes and generalizes published data on the catalytic syntheses of six-, seven-, and eight-membered S,N-heterocycles and O,N-, S,N-, and O,S,N-macroheterocycles.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Rathore, B.S. and Kumar, M., Bioorg. Med. Chem., 2006, vol. 14, p. 5678.
Barazarte, A., Bioorg. Med. Chem., 2008, vol. 16, p. 3661.
Chia, E.W., Bioorg. Med. Chem., 2008, vol. 16, p. 9432.
Holla, B.S., Vereendra, B., Shivananda, M.K., and Poojary, B., Eur. J. Med. Chem., 2003, vol. 38, p.759.
Fringuelli, R., Schiaffella, F., Bistoni, F., Pitzurra, L., and Vecchiarelli, A., Bioorg. Med. Chem., 1998, vol. 6, p.103.
Parai, M.K. and Panda, G., Tetrahedron Lett., 2009, vol. 50, p. 4703.
Malakar, C.C., Merisor, E., Conrad, J., and Beifuss, U., Synlett, 2010, vol. 12, p. 1766.
Mukherjee, C. and Biehl, E., Heterocycles, 2004, vol. 63, p. 2309.
Gowda, J., Khader, A.M.A., Kalluraya, B., Shree, P., and Shabaraya, A.R., Eur. J. Med. Chem., 2011, vol. 46, p. 4100.
Chhikara, B.S., Tandon, V., and Mishra, A.K., Heterocycl. Commun., 2004, vol. 10, p.441.
Grevtsov, O.Y., Zaremba, O.V., Bondarenko, A.B., Drushlyak, O.G., Kovalenko, S.M., and Chernykh, V.P., Int. J. Org. Chem., 2013, vol. 3, p.125.
Korth, C., May, B.C.H., Cohen, F.E., and Prusiner, S.B., Proc. Natl. Acad. Sci. U. S. A., 2001, vol. 98, p. 9836.
Melvin, J.Y. and Jefferson, R.M., J. Med. Chem., 1992, vol. 35, p.716.
Basta-Kaim, A., Budziszewska, B., Jaworska-Feil, L., Tetich, M., Kubera, M., Leskiewicz, M., Otczyk, M., and Lason, W., Neuropsychopharmacology, 2006, vol. 31, p.853.
Ma, D.-W., Geng, Q., Zhang, H., and Jiang, Y.-W., Angew. Chem., Int. Ed., 2010, vol. 49, p. 1291.
Dahl, T., Tornoe, S.W., Bang-Andersen, B., Nielsen, P., and Jorgensen, M., Angew. Chem., Int. Ed., 2008, vol. 47, p. 1726.
Mayer, M., Lang, P.T., Gerber, S., Madrid, P.B., Pinto, I.G., Guy, R.K., and James, T.L., Chem. Biol., 2006, vol. 13, p.993.
Silva, G.A., Costa, L.M.M., Brito, F.C.F., Miranda, A.L.P., Barreiro, E.J., and Fraga, C.A.M., Bioorg. Med. Chem., 2004, vol. 12, p. 3149.
Filip, S.V., Silberg, I.A., Surducan, E., Vlassa, M., and Surducan, V., Synth. Commun., 1998, vol. 28, p.337.
Tao, S., Lv, A., Zhao, N., Yang, S., Liu, X., Zhou, J., Liu, W., and Zhao, J., Synlett, 2011, no. 1, p.134.
Dai, S., Sun, X., Tu, X., Wu, L., Zhan, D., and Zeng, Q., Chem. Commun., 2012, vol. 48, p. 5367.
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya volna, 2008, 16th ed.
Kubo, H., Sato, R., Hamura, I., and Ohi, T., J. Agric. Food Chem., 1970, vol. 18, p.60.
Chapleo, C.B., Myers, M., Saville, J.F., Smith, A.C.B., Stilling, M.R., Tulloch, I.F., Walter, D.S., and Welboum, A.P., J. Med. Chem., 1986, vol. 29, p. 2273.
Turner, S., Myers, M., Gadie, B., Hale, S.A., Horsley, A., Nelsen, A.J., Pape, R., Saville, J.F., Doxey, J.C., and Berridge, T.L., J. Med. Chem., 1988, vol. 31, p.906.
Oruc, E.E., Rollas, S., Kandemirli, F., Shvets, N., and Dimoglo, A.S., J. Med. Chem., 2004, vol. 47, p. 6760.
Kamal, A., Hetercycles, 1990, vol. 31, p. 1377.
Yadav, L.D.S., Vaish, A., and Sharma, S., J. Agric. Food Chem., 1994, vol. 42, p.811.
Ozcelik, A.B., Ersan, S., Ural, A.U., Ozkan, S., and Ertan, M., Arzneim. Forsch., 2007, vol. 57, p.554.
Hussein, M.A. and Hashem, M., Arch. Pharm., 2008, vol. 341, p.370.
Akhmetova, V.R., Nadyrgulova, G.R., Tyumkina, T.V., Starikova, Z.A., Golovanov, D.G., Antipin, M.Yu., Kunakova, R.V., and Dzhemilev, U.M., Russ. Chem. Bull., Int. Ed., 2006, vol. 55, no. 10, p. 1824.
Akhmetova, V.R., Khairullina, R.R., Tyumkina, T.V., Nelyubina, Yu.V., Smolyakov, A.F., Bushmarinov, I.S., Starikova, Z.A., Abdullin, M.F., and Kunakova, R.V., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 2, p.425.
Akhmetova, V.R., Khairullina, R.R., Nadyrgulova, G.R., Kunakova, R.V., and Dzhemilev, U.M., Russ. J. Org. Chem., 2008, vol. 44, p.190.
Niatshina, Z.T., Murzakova, N.N., Vasilieva, I.V., Rakhimova, E.B, Akhmetova, V.R., and Ibragimov, A.G., Arkivoc, 2011, part (viii), p.141.
Murzakova, N.N., Rakhimova, E.B., Vasil’yeva, I.V., Prokof’yev, K.I., Akhmetova, V.R., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2011, vol. 52, p. 4090.
Rakhimova, E.B., Vasil’eva, I.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2011, vol. 47, p. 1300.
Ozden, I.V., Cand. Sci. (Chem.) Dissertation, Ufa, 2016.
Fodor, L., Szabo, J., Bernath, G., and Sohar, P., Tetrahedron Lett., 1995, vol. 36, p.753.
Pei, Y., Lilly, M.J., Owen, D.J., D’Souza, L.J., Tang, X.-Q., Yu, J., Nazarbaghi, R., Hunter, A., Anderson, C.M., Glasco, S., Ede, N.J., James, I.W., Maitra, U., Chandrasekan, S., Moos, W.H., and Ghosh, S.S., J. Org. Chem., 2003, vol. 68, p.92.
Bates, D.K. and Li, K., J. Org. Chem., 2002, vol. 67, p. 8662.
Marcaccini, R., Miguel, D., Torroba, T., and Garcia-Valverde, M., J. Org. Chem., 2003, vol. 68, p. 3315.
Chen, S.Q., Ding, F., Zhang, Y.C., and Liu, F.M., J. Chem. Crystallogr., 2011, vol. 41, p.514.
Naik, T.R.R., Naik, H.S.B., Raghavendra, M., Bindu, P.J., and Mahadevan, K.M., J. Sulfur Chem., 2007, vol. 28, p.589.
Karikomi, M., D’Hooghe, M., Verniest, G., and De Kimpe, N., Org. Biomol. Chem., 2008, vol. 6, p. 1902.
Vega, J.A., Cueto, S., Ramos, A., Vaquero, J.J., Garcia-Navio, J.L., and Alvarez-Builla, J., Tetrahedron Lett., 1996, vol. 37, p. 6413.
Besson, T. and Thiéry, V., Microwave-Assisted Synthesis of Heterocycles, van der Eycken, E. and Kappe, C.O., Eds., Berlin: Springer, 2006, vol. 1, p.59.
Ham, W.-H., Oh, C.-Y., Lim, T.-G., Jung, Y.-H., and Jung, Y.H., Arch. Pharmacal Res., 1995, vol. 18, p.366.
Dabiri, M., Salehi, P., Bahramnejad, M., and Baghbanzadeh, M., Monatsh. Chem., 2012, vol. 143, p.109.
Wu, L.-Y., Lu, K., Desai, M., Packiarajan, M., Joshi, A., Marzabadi, M.R., Jubian, V., Andersen, K., Chandrasena, G., Boyle, N.J., and Walker, M.W., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 5573.
Tseng, T.C. and Wu, M.J., Tetrahedron: Asymmetry, 1995, vol. 6, p. 1633.
Bartolozzi, A., Foudoulakis, H.M., and Cole, B.M., Synthesis, 2008, no. 13, p. 2023.
Hansson, L., Hedner, T., Lund-Johansen, P.., Kjeldsen, S.E., Lindholm, L.H., Syvertsen, J. O., Lanke, J., de Faire, U., Dahlöf, B., and Karlberg, B.E., Lancet, 2000, vol. 356, p.359.
Murzakova, N.N., Prokof’ev, K.I., Tyumkina, T.V., and Ibragimov, A.G., Russ. J. Org. Chem., 2012, vol. 48, p.588.
Makhmudiyarova, N.N., Rakhimov, R.Sh., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2014, vol. 50, p.187.
Khairullina, R.R., Akmanov, B.F., Kunakova, R.V., Ibragimov, A.G., and Dzhemilev, U.M., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, no. 1, p.98.
Makhmudiyarova, N.N., Prokof’ev, K.I., Mudarisova, L.V., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2013, vol. 49, p.658.
Dorokhov, V.I. and Vovk, M.V., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1993, vol. 36, p.82.
Tsotinis, A., Eleutheriades, A., Di Bari, L., and Pescitelli, G., J. Org. Chem., 2007, vol. 72, p. 8928.
Rakhimova, E.B., Vasil’eva, I.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Chem. Heterocycl. Compd., 2012, vol. 48, no. 7, p. 1050.
Khairullina, R.R., Akmanov, B.F., Starikova, Z.A., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2013, vol. 49, p. 1686.
Rakhimova, E.B., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2014, vol. 50, p. 1613.
Rakhimova, E.B., Ozden, I.V., Meshcheryakova, E.S., Khalilov, L.M., and Ibragimov, A.G., Russ. J. Org. Chem., 2015, vol. 51, p. 1788.
Lu, M. and Alper, H., J. Am. Chem. Soc., 2005, vol. 127, p. 14776.
Kuti, M., Rabai, J., Kapovits, I., Jalsovszky, I., Argay, G., Kalman, A., and Parkanyi, L., J. Mol. Struct., 1996, vol. 382, p.1.
Krishnamurti, R., Nagy, S., and Smolka, T.F., US Patent no. 5 621 153 A (1997); Chem. Abstr., 1997, vol. 126, no. 330629.
Bates, D.K. and Li, K., J. Org. Chem., 2002, vol. 67, p. 8662.
Makhmudiyarova, N.N., Prokof’ev, K.I., Mudarisova, L.V., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2013, vol. 49, p.655.
Yordanov, A.T. and Roundhill, D.M., Coord. Chem. Rev., 1998, vol. 170, p.93.
Gloe, K., Graubaum, H., Wust, M., Rambusch, T., and Seichter, W., Coord. Chem. Rev., 2001, vol. 222, p.103.
Cation Binding by Macrocycles, Inoue, Y. and Gokel, G.W., Eds., New York: Marcel Dekker, 1990.
Buhlmann, P., Pretsch, E., and Bakker, E., Chem. Rev., 1998, vol. 98, p. 1593.
Valeur, B. and Leray, I., Coord. Chem. Rev., 2000, vol. 205, p.3.
Feiters, M.C., Comprehensive Supramolecular Chemistry, Atwood, J.L., Lehn, J.-M., and Reinhoudt, D.N., Eds., Pergamon: Oxford, 1996, vol. 10, p.267.
Mbatia, H.W., Kennedy, D.P., Camire, C.E., Incarvito, C.D., and Burdette, S.C., Eur. J. Inorg. Chem., 2010, vol. 32, p. 5069.
Yakushev, A.A., Averin, A.D., Anokhin, M.V., Maloshitskaya, O.A., Lamati, F., and Beletskaya, I.P., Macroheterocycles, 2014, vol. 7, no. 4, p.358.
Yakushev, A.A., Anokhin, M.V., Averin, A.D., Maloshitskaya, O.A., Savelyev, E.N., Butov, G.M., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Macroheterocycles, 2013, vol. 6, no. 1, p.40.
Kobelev, S.M., Averin, A.D., Buryak, A.K., Denat, F., Guilard, R., and Beletskaya, I.P., Macroheterocycles, 2014, vol. 7, no. 1, p.28.
Weitz, E.A. and Pierre, V.C., Chem. Commun., 2011, vol. 47, p.541.
Arnaud, N., Picard, C., Cazaux, L., and Tisnes, P., Tetrahedron Lett., 1995, vol. 36, p. 5531.
Khairullina, R.R., Akmanov, B.F., Tyumkina, T.V., Talipova, R.R., Ibragimov, A.G., and Dzhemilev, U.M., Macroheterocycles, 2015, vol. 8, p.89.
Ibragimov, A.G., Dzhemilev, U.M., Rakhimova, E.B., and Vasil’eva, I.V., RU Patent no. 2 538 595, 2015; Byull. Izobret., 2015, no.1.
Upadhyay, D.N., Agarwal, N., Goel, A., and Ram, V.J., J. Chem. Res., 2003, no. 6, p.380.
Sakamoto, H., Ishikawa, J., and Otomo, M., Bull. Chem. Soc. Jpn., 1995, vol. 68, p. 2831.
Ishikawa, J., Sakamoto, H., Mizuno, T., and Otomo, M., Bull. Chem. Soc. Jpn., 2006, vol. 68, p. 3071.
Makhmudiyarova, N.N., Mudarisova, L.V., Meshcheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2015, vol. 71, p.259.
Makhmudiyarova, N.N., Mudarisova, L.V., Tyumkina, T.V., Yanybin, V.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2015, vol. 56, p. 3820.
Glenny, M.W., van de Water, L.G.A., Vere, J.M., Blake, A.J., Wilson, C., Driessen, W.L., Reedijk, J., and Schroder, M., Polyhedron., 2006, vol. 25, p.599.
Pop, A.M., PhD Thesis, Cluj-Napoca, România, 2012.
Rakhimova, E.B., Ozden, I.V., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2016, vol. 52, p.571.
Tian, M., Ihmels, H., and Benner, K., Chem. Commun., 2010, vol. 46, p. 5719.
Bradsher, C.K., Sherer, J.P., and Parham, J.H., J. Chem. Eng. Data, 1965, vol. 10, p.180.
Tanaka, M., Nakamura, M., Ikeda, T., Ikeda, K., Ando, H., Shibutani, Y., Yajima, S., and Kimura, K., J. Org. Chem., 2001, vol. 66, p. 7008.
Tian, M. and Ihmels, H., Chem. Commun., 2009, no. 22, p. 3175.
Granzhan, A., Ihmels, H., and Tian, M., Arkivoc, 2015, part (vi), p.494.
Abalos, T., Jimenez, D., Martínez-Mañez, R., Ros-Lis, J.V., Royo, S., Sancenón, F., Soto, J., Costero, A.M., Gil, S., and Parra, M., Tetrahedron Lett., 2009, vol. 50, p. 3885.
Jiménez, D., Martínez-Máñez, R., Sancenón, F., Ros-Lis, J.V., Soto, J., Benito, Á., and García-Breijo, E., Eur. J. Inorg. Chem., 2005, no. 12, p. 2393.
Kütük, I., M. Sc. Thesis, Middle East Technical University, 2008.
Tulyakova, E.V., Fedorova, O.A., Fedorov, Yu.V., Jonusauskas, G., Kuz’mina, L.G., Howard, J.A.K., and Anisimov, A.V., Russ. Chem. Bull., Int. Ed., 2007, vol. 56, no. 3, p.513.
Selektor, S.L., Raitman, O.A., Silant’eva, D.A., Ivanova, N.V., Yonusauskas, G., Lukovskaya, E.V., Batat, P., and Arslanov, V.V., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, p.484.
Makhmudiyarova, N.N., Khatmullina, G.M., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Arkivoc, 2016, part (iii), p. 48.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.B. Rakhimova, I.V. Ozden, A.G. Ibragimov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 7, pp. 959–984.
Rights and permissions
About this article
Cite this article
Rakhimova, E.B., Ozden, I.V. & Ibragimov, A.G. Catalysis in the Synthesis of S,N-Heterocycles and O,N-, S,N-, and O,S,N-Macroheterocycles. Russ J Org Chem 54, 961–986 (2018). https://doi.org/10.1134/S1070428018070011
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018070011