Abstract
The review summarizes methods for the synthesis of benzo-fused heterocyclic compounds containing a fairly stable exocyclic double bond in a saturated hetero- or polyheterocyclic fragment. Examples of using such compounds for the preparation of biologically active substances and heterocycles for other applications are given.
Similar content being viewed by others
References
Bharkavi, C., Kumar, S.V., Ali, M.A., Osman, H., Muthusubramanian, S., and Perumal, S., Bioorg. Med. Chem., 2016, vol. 24, p. 5873.
Hu, S., Wang, B., Zhang, Y., Tang, W., Fang, M., Lu, T., and Du, D., Org. Biomol. Chem., 2015, vol. 13, p. 4661.
He, F., Bo, Y., Altom, J.D., and Corey, E.J., J. Am. Chem. Soc., 1999, vol. 121, p. 6771.
Sapeta, K. and Kerr, M.A., Org. Lett., 2009, vol. 11, p. 2081.
Crawley, S.L. and Funk, R.L., Org. Lett., 2006, vol. 8, p. 3995.
Numata, A., Takahashi, C., Ito, Y., Takada, T., Kawai, K., Usami, Y., Matsumura, E., Imachi, M., Ito, T., and Hasegawa, T., Tetrahedron Lett., 1993, vol. 34, p. 2355.
Shinya, K., Furihata, K., Teshima, Y., Hayakawa, Y., and Seto, H., J. Org. Chem., 1993, vol. 58, p. 4170.
Turk, C.F., Krapcho, J., Michel, I.M., and Weinryb, I., J. Med. Chem., 1977, vol. 20, p. 729.
Komagata, D., Sawa, T., Muraoka, Y., Imada, C., Okami, Y., and Takeuchi, T., J. Antibiot., 1992, vol. 45, p. 1117.
Miles, D.H., Petrovna, K.O., Naser, S., Yurjevich, S.S., Goun, E.A., and Michailovich, S.V., US Patent no. 6 649 610, 2003; Chem. Abstr., 2003, vol. 139, no. 381 495 j.
Zhou, L., Yang, J.-S., Wu, X., Zou, J.-H., Xu, X.-D., and Tu, G.-Z., Heterocycles, 2005, vol. 65, p. 1409.
Kam, T.-S., Tan, S.-J., Ng, S.-K., and Komiyama, K., Org. Lett., 2008, vol. 10, p. 3749.
Stevenson, C.S., Capper, E.A., Roshak, A.K., Marquez, B., Eichman, C., Jackson, J.R., Mattern, M., Gerwick, W.H., Jacobs, R.S., and Marshall, L.A., J. Pharmacol. Exp. Ther., 2009, vol. 303, p. 858.
Subramaniam, G., Hiraku, O., Hayashi, M., Koyano, T., Komiyama, K., and Kam, T.-S., J. Nat. Prod., 2007, vol. 70, p. 1783.
Dugan, J.J., Hesse, M., Renner, U., and Schmid, H., Helv. Chim. Acta, 1969, vol. 52, p. 701.
Renner, U., Prins, D.A., Burlingame, A.L., and Biemann, K., Helv. Chim. Acta, 1963, vol. 46, p. 2186.
Jagetia, G., Baliga, M.S., Venkatesh, P., Ulloor, J.N., Mantena, S.K., Genebriera, J., and Mathuram, V., J. Pharm. Pharmacol., 2005, vol. 57, p. 1213.
Goodson, J.A., J. Chem. Soc., 1932, vol. 127, p. 2626.
Girardot, M., Gadea, A., Deregnaucourt, C., Deville, A., Dubost, L., Nay, B., Maciuk, A., Rasoanaivo, P., and Mambu, L., Eur. J. Org. Chem., 2012, p. 2816.
Benbow, J.W. and Schulle, G.K., Angew. Chem., Int. Ed. Engl., 1992, vol. 31, p. 915.
Trost, B.M., O’Boyle, B.M., Torres, W., and Ameriks, M.K., Chem. Eur. J., 2011, vol. 17, p. 7890.
Uchida, I., Takase, S., Kayakiri, H., Kiyoto, S., Hashimoto, M., Tada, T., Koda, S., and Morimoto, Y., J. Am. Chem. Soc., 1987, vol. 109, p. 4108.
He, X., Hu, S., Liu, K., Guo, Y., Xu, J., and Shao, S., Org. Lett., 2006, vol. 8, p. 333.
Wang, L., He, X., Guo, Y., Xu, J., and Shao, S., Org. Biomol. Chem., 2011, vol. 9, p. 752.
Krishna, C.T. and Rajagopal, N., Synlett, 2011, p. 2559.
Zhu, X.-Q., Wu, J.-S., and Xie, J.-W., Tetrahedron, 2016, vol. 72, p. 8327.
Harrison, C.A., Leineweber, R., Moody, C.J., and Williams, J.M.J., J. Chem. Soc., Perkin Trans. 1, 1995, p. 1127.
Barluenga, J., Fañanás, F.J., Sanz, R., and Fernández, Y., Chem. Eur. J., 2002, vol. 8, p. 2034.
Wojciechowski, K., Eur. J. Org. Chem., 2001, p. 3587.
Laronze, M. and Sapi, J., Tetrahedron Lett., 2002, vol. 43, p. 7925.
Ko, C.-W. and Chou, T., J. Org. Chem., 1998, vol. 63, p. 4645.
Li, Z., Kumar, A., Sharma, S.K., Parmar, V.S., and Van der Eycken, E.V., Tetrahedron, 2015, vol. 71, p. 3333.
Safrygin, A.V., Irgashev, R.A., Slepukhin, P.A., Roschenthaler, G.-V., and Sosnovskikh, V.Y., Tetrahedron, 2015, vol. 71, p. 8535.
Han, B., Xiao, Y.-C., Yao, Y., and Chen, Y.-C., Angew. Chem., 2010, vol. 122, p. 10.387.
Ferrer, C. and Echavarren, A.M., Angew. Chem., Int. Ed., 2006, vol. 45, p. 1105.
Ferrer, C., Amijs, C.H.M., and Echavarren, A.M., Chem. Eur. J., 2007, vol. 13, p. 1358.
Likhacheva, N.A., Gataullin, R.R., Abdrakhmanov, I.B., and Tolstikov, G.A., Azotsoderzhashchie geterotsikly (Nitrogen-Containing Heterocycles), Kartsev, V.G., Ed., Moscow: Iridium, 2006, vol. 1, p. 353.
Terada, Y., Arisawa, M., and Nishida, A., J. Org. Chem., 2006, vol. 71, p. 1269.
Arisawa, M., Terada, Y., Takahashi, K., Nakagawa, M., and Nishida, A., J. Org. Chem., 2006, vol. 71, p. 4255.
Matsumoto, S., Samata, D., Akazome, M., and Ogura, K., Tetrahedron Lett., 2009, vol. 50, p. 111.
Terada, Y., Arisawa, M., and Nishida, A., Angew. Chem., 2004, vol. 116, p. 4155.
Ogawa, T., Nakamura, T., Araki, T., Yamamoto, K., Shuto, S., and Arisawa, M., Eur. J. Org. Chem., 2012, p. 3084.
Larock, R.C., Hightower, T.R., Hasvold, L.A., and Peterson, K.R., J. Org. Chem., 1996, vol. 61, p. 3584.
Larock, R.C., Pace, P., Yang, H., and Russell, C.E., Tetrahedron, 1998, vol. 54, p. 9961.
Sakamoto, T., Kondo, Y., Uchiyama, M., and Yamanaka, H., J. Chem. Soc., Perkin Trans. 1, 1993, p. 1941.
Muzart, J., Tetrahedron, 2009, vol. 65, p. 8313.
Skladchikov, D.A. and Gataullin, R.R., Russ. J. Gen. Chem., 2013, vol. 83, p. 373.
Lhermet, R., Durandetti, M., and Maddaluno, J., Beilstein J. Org. Chem., 2013, vol. 9, p. 710.
Charrier, N., Demont, E., Dunsdon, R., Maile, G., Naylor, A., O’Brien, A., Redshaw, S., Theobald, P., Vesey, D., and Walter, D., Synlett, 2005, p. 3071.
Hegedus, L.S., Mulhern, T.A., and Mori, A., J. Org. Chem., 1985, vol. 50, p. 4282.
Lin, H. and Kazmaier, U., Eur. J. Org. Chem., 2009, p. 1221.
Murphy, J.A., Scot, K.A., Sinclan, R.S., and Lewis, N., Tetrahedron Lett., 1997, vol. 38, p. 7295.
Strat, F.L. and Maddaluno, J., Org. Lett., 2002, vol. 4, p. 2791.
Kim, H.S., Lee, H.S., Kim, S.H., and Kim, J.N., Tetrahedron Lett., 2009, vol. 50, p. 3154.
Beemelmanns, C. and Reissig, H.-U., Org. Biomol. Chem., 2009, vol. 7, p. 4475.
Petkovic, M., Nasufovic, V., Djukanovic, D., Vujosevic, Z.T., Jadranin, M., Matovic, R., and Savic, V., Eur. J. Org. Chem., 2016, p. 1279.
Camp, J.E., Craig, D., Funai, K., and White, A.J.P., Org. Biomol. Chem., 2011, vol. 9, p. 7904.
Junji, I., Takashi, M., and Yu, I., Chem. Lett., 2004, vol. 33, p. 1354.
Baxter, C.A., Cleator, E., Alam, M., Daves, A.J., Goodyear, A., and O’Hagen, M., Org. Lett., 2010, vol. 12, p. 668.
Gataullin, R.R., Afon’kin, I.S., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Mendeleev Commun., 2001, p. 201.
Gataullin, R.R., Sotnikov, A.M., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2005, vol. 41, p. 715.
Yao, T. and Larock, R.C., J. Org. Chem., 2005, vol. 70, p. 1432.
Bantreil, X., Bourderioux, A., Mateo, P., Hagerman, C.E., Selkti, M., Brachet, E., and Belmont, P., Org. Lett., 2016, vol. 18, p. 4814.
Vasilevskii, S.F., Mikhailovskaya, T.F., Stepanov, A.A., Mamatyuk, V.I., and Fadeev, D.S., Russ. J. Org. Chem., 2014, vol. 50, p. 506.
Perdigao, G., Deraeve, C., Mori, G., Pasca, M.R., Pratviel, G., and Bernardes-Genisson, V., Tetrahedron, 2015, vol. 71, p. 1555.
Chen, H., Wang, Q., and Huang, Y., Tetrahedron, 2015, vol. 71, p. 3632.
Reddy, V., Jadhav, A.S., and Anand, R.V., Eur. J. Org. Chem., 2016, p. 453.
Li, D.Y., Shi, K.J., Mao, X.F., Zhao, Z.L., Wu, X.Y., and Liu, P.N., Tetrahedron, 2014, vol. 70, p. 7022.
Yamskov, A.N., Samet, A.V., and Semenov, V.V., Russ. Chem. Bull., Int. Ed., 2003, vol. 52, p. 759.
Skorcz, J.A. and Suh, J.T., US Patent no. 3 472 843 A. www.google.com/patents/US3472843.
Cao, G., Long, F., Zhao, Y., Wang, Y., Huang, L., and Teng, D., Tetrahedron, 2014, vol. 70, p. 9359.
Chen, X., Fan, H., Zhang, S., Yu, C., and Wang, W., Chem. Eur. J., 2016, vol. 22, p. 716.
Larock, R.C., Berrios-Pena, N.G., and Fried, C.A., J. Org. Chem., 1991, vol. 56, p. 2615.
Larock, R.C. and Zenner, J.M., J. Org. Chem., 1995, vol. 60, p. 482.
Zenner, J.M. and Larock, R.C., J. Org. Chem., 1999, vol. 64, p. 7312.
Ma, J., Yin, W., Zhou, H., Liao, X., and Cook, J.M., J. Org. Chem., 2009, vol. 74, p. 264.
Fujita, T., Sugiyama, K., Sanada, S., Ichitsuka, T., and Ichikawa, J., Org. Lett., 2016, vol. 18, p. 248.
Dethe, D.H. and Boda, R., Chem. Eur. J., 2016, vol. 22, p. 106.
Zhou, X., Peng, Z., Zhao, H., Zhang, Z., Lu, P., and Wang, Y., Chem. Commun., 2016, vol. 52, p. 10.676.
Kato, Y., Ebiike, H., Achiwa, K., Ashizawa, N., Kurihara, T., and Kobayashi, F., Chem. Pharm. Bull., 1990, vol. 38, p. 2060.
Pathare, R.S., Sharma, S., Elagandhula, S., Saini, V., Sawant, D.M., Yadav, M., Sharon, A., Khan, S., and Pardasani, R.T., Eur. J. Org. Chem., 2016, p. 5579.
Kato, Y., Takemoto, M., and Achiwa, K., Chem. Pharm. Bull., 1993, vol. 41, p. 2003.
Munoz, S.B., Aloia, A.N., Moore, A.K., Papp, A., Mathew, T., Fustero, S., Olah, G.A., and Prakash, G.K.S., Org. Biomol. Chem., 2016, vol. 14, p. 85.
Zheng, X.-X., Du, C., Zhao, X.-M., Zhu, X., Suo, J.-F., Hao, X.-Q., Niu, J.-L., and Song, M.-P., J. Org. Chem., 2016, vol. 81, p. 4002.
Reddy, M.C. and Jeganmohan, M., Org. Lett., 2014, vol. 16, p. 4866.
Mazgarova, G.G., Suponitskii, K.Yu., and Gataullin, R.R., Russ. J. Org. Chem., 2013, vol. 49, p. 1322.
Mazgarova, G.G., Absalyamova, A.M., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 1200.
Kuroda, N., Takahashi, Y., Yoshinaga, K., and Mukai, C., Org. Lett., 2006, vol. 8, p. 1843.
Inagaki, F., Mizutani, M., Kuroda, N., and Mukai, C., J. Org. Chem., 2009, vol. 74, p. 6402.
Marinelli, E.R., Tetrahedron Lett., 1982, vol. 23, p. 2745.
Susanti, D., Koh, F., Kusuma, J.A., Kothandaraman, P., and Chan, P.W.H., J. Org. Chem., 2012, vol. 77, p. 7166.
Kumar, G.R., Kumar, Y.K., Kant, R., and Reddy, M.S., Org. Biomol. Chem., 2016, vol. 14, p. 4077.
Manisha, M., Dhiman, S., Mathew, I., and Ramasastry, S.S.V., Org. Biomol. Chem., 2016, vol. 14, p. 5563.
Xu, X.-L., Yu, C.-L., Chen, W., Li, Y.-C., Yang, L.-J., Li, Y., Zhang, H.-B., and Yang, X.-D., Org. Biomol. Chem., 2015, vol. 13, p. 1550.
Nani, R.R., Shaum, J.B., Gorkaand, A.P., and Schnermann, M.J., Org. Lett., 2015, vol. 17, p. 302.
Xiao, H., Li, P., Zhang, S., Zhang, W., Zhang, W., and Tang, B., Chem. Commun., 2016, vol. 52, p. 12.741.
Chao, S., Krejci, E., Bernard, V., Leroy, J., Jean, L., and Renard, P.-Y., Chem. Commun., 2016, vol. 52, p. 11.599.
Gorka, A.P., Nani, R.R., and Schnermann, M.J., Org. Biomol. Chem., 2015, vol. 13, p. 7584.
Tirla, A. and Rivera-Fuentes, P., Angew. Chem., Int. Ed., 2016, vol. 55, p. 14.709.
Matsui, M., Ando, S., Fukushima, M., Shibata, T., Kubota, Y., and Funabiki, K., Tetrahedron, 2015, vol. 71, p. 3528.
Yang, L., Huang, W., He, X.-H., Yang, M.-C., Li, X., He, G., Peng, C., and Han, B., Adv. Synth. Catal., 2016, vol. 358, p. 2970.
Liang, J., Zhang, H.-H., Wang, C.-S., Wu, Q., and Shi, F., Synthesis, 2016, vol. 48, p. 4548.
Lu, B. and Ma, D., Org. Lett., 2006, vol. 8, p. 6115.
Millemaggi, A., Perry, A., Whitwood, A.C., and Taylor, R.J.K., Eur. J. Org. Chem., 2009, p. 2947.
Ashimori, A., Bachand, B., Overman, L.E., and Poon, D.J., J. Am. Chem. Soc., 1998, vol. 120, p. 6477.
Ashimori, A., Bachand, B., Galter, M.A., Govek, S.P., Overman, L.E., and Poon, D.J., J. Am. Chem. Soc., 1998, vol. 120, p. 6488.
Terpko, M.O. and Hesk, R.F., J. Am. Chem. Soc., 1979, vol. 101, p. 5281.
Mori, M. and Ban, Y., Tetrahedron Lett., 1979, vol. 13, p. 1133.
Inoue, M., Takahashi, T., Furuyama, H., and Hirama, M., Synlett, 2006, p. 3037.
Yamamoto, Y., Chem. Soc. Rev., 2014, vol. 43, p. 1575.
Tang, S., Peng, P., Wang, Z.Q., Tang, B.X., Deng, C.L., Li, J.H., Zhong, P., and Wang, N.X., Org. Lett., 2008, vol. 10, p. 1875.
Jiang, T.-S., Tang, R.-Y., Zhang, X.-G., Li, X.-H., and Li, J.-H., J. Org. Chem., 2009, vol. 74, p. 8834.
Reiko, Y., Shingo, O., Tsubasa, I., Kazuo, Y., Masayuki, Y., Shunsaku, O., and Yoshiji, T., J. Org. Chem., 2005, vol. 70, p. 6972.
D’Souza, D.M., Rominger, F., and Muller, T.J.J., Angew. Chem., Int. Ed., 2005, vol. 44, p. 153.
Reiko, Y., Shingo, O., Munetako, O., and Yoshiji, T., Org. Lett., 2004, vol. 6, p. 2825.
Pinto, A., Neuville, L., Retailleu, P., and Zhu, J., Org. Lett., 2006, vol. 8, p. 4927.
Shintani, R., Yamagami, T., and Hayashi, T., Org. Lett., 2006, vol. 8, p. 4799.
Miura, T., Takahashi, Y., and Murakami, M., Org. Lett., 2008, vol. 10, p. 1743.
Kobayashi, Y., Kamisari, H., Yanada, R., and Takemoto, Y., Org. Lett., 2006, vol. 8, p. 2711.
Xie, J., Xing, X.-Y., Sha, F., Wu, Z.-Y., and Wu, X.-Y., Org. Biomol. Chem., 2016, vol. 14, p. 8346.
Ölgena, S. and Özkan, S., Z. Naturforsch., Teil C, 2009, vol. 64, p. 155.
Robinson, R.P., Reiter, L.A., Barth, W.E., Campeta, A.M., Cooper, K., Cronin, B.J., Destito, R., Donahue, K.M., Falkner, F.C., Fiese, E.F., Johnson, D.L., Kuperman, A.V., Liston, T.E., Malloy, D., Martin, J.J., Mitchell, D.Y., Rusek, F.W., Shamblin, S.L., and Wright, C.F., J. Med. Chem., 1996, vol. 39, p. 10.
Mendel, D.B., Laird, A.D., Smolich, B.D., Blake, R.A., Liang, C., Hannah, A.L., Shaheen, R.M., Ellis, L.M., Weitman, S., Shawver, L.K., and Cherrington, J.M., Anticancer Drug Des., 2000, vol. 15, p. 29.
Le Tourneau, C., Raymond, E., and Faivre, S., Ther. Clin. Risk Manage., 2007, vol. 3, p. 341.
Chen, Z., Merta, P.J., Lin, N.-H., Tahir, S.K., Kovar, P., Sham, H.L., and Zhang, H., Mol. Cancer Ther., 2005, vol. 4, p. 562.
Kumar, G.B., Nayak, V.L., Bin Sayeed, I., Reddy, V.S., Shaik, A.B., Mahesh, R., Baig, M.F., Shareef, M.A., Ravikumar, A., and Kamal, A., Bioorg. Med. Chem., 2016, vol. 24, p. 1729.
Liang, Y.-R., Chen, X.-Y., Wu, Q., and Lin, X.-F., Tetrahedron, 2015, vol. 71, p. 616.
Muthusamy, S. and Kumar, S.G., Tetrahedron, 2016, vol. 72, p. 2392.
Jiang, Y.-H. and Yan, C.-G., Synthesis, 2016, vol. 48, p. 3057.
Zhao, H., Wang, X., Wang, L., and Xiao, J., Synthesis, 2016, vol. 48, p. 2112.
Zheng, C., Chen, W.-X., and Chen, F.-E., Asian J. Org. Chem., 2015, vol. 4, p. 1044.
Zheng, C., Wang, H.-F., Chen, W.-Q., Chen, W.-X., and Chen, F.-E., Asian J. Org. Chem., 2015, vol. 4, p. 619.
Li, S.-W., Liu, Y., Sampson, P.B., Patel, N.K., Forrest, B.T., Edwards, L., Laufer, R., Feher, M., Ban, F., Awrey, D.E., Hodgson, R., Beletskaya, I., Mao, G., Mason, J.M., Wei, X., Luo, X., Kiarash, R., Green, E., Mak, T.W., Pan, G., and Pauls, H.W., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 4625.
Sampson, P.B., Liu, Y., Patel, N.K., Feher, M., Forrest, B., Li, S.-W., Edwards, L., Laufer, R., Lang, Y., Ban, F., Awrey, D.E., Mao, G., Plotnikova, O., Leung, G., Hodgson, R., Mason, J., Wei, X., Kiarash, R., Green, E., Qiu, W., Chirgadze, N.Y., Mak, T.W., Pan, G., and Pauls, H.W., J. Med. Chem., 2015, vol. 58, p. 130.
Barkov, A.Yu., Zimnitskiy, N.S., Korotaev, V.Yu., Kutyashev, I.V., Moshkin, V.S., and Sosnovskikh, V.Ya., Tetrahedron, 2016, vol. 72, p. 6825.
Rajasekaran, T., Sridhar, B., and Reddy, B.V.S., Tetrahedron, 2016, vol. 72, p. 2102.
Vetica, F., de Figueiredo, R.M., Orsini, M., Tofani, D., and Gasperi, T., Synthesis, 2015, vol. 47, p. 2139.
Grigg, R., Millington, E.L., and Thornton-Pett, M., Tetrahedron Lett., 2002, vol. 43, p. 2605.
Velikorodov, A.V., Poddubnyi, O.Yu., Ionova, V.A., and Titova, O.L., Russ. J. Org. Chem., 2011, vol. 47, p. 1596.
Sun, J., Chen, L., Gong, H., and Yan, C.-G., Org. Biomol. Chem., 2015, vol. 13, p. 5905.
Velikorodov, A.V., Poddubnyi, O.Yu., Krivosheev, O.O., and Titova, O.L., Russ. J. Org. Chem., 2011, vol. 47, p. 402.
Velikorodov, A.V., Poddubnyi, O.Yu., Kuanchalieva, A.K., and Krivosheev, O.O., Russ. J. Org. Chem., 2010, vol. 46, p. 1826.
Velikorodov, A.V., Imasheva, A.K., Kuanchalieva, A.K., and Poddubnyi, O.Yu., Russ. J. Org. Chem., 2010, vol. 46, p. 971.
Velikorodov, A.V., Kuanchalieva, A.K., and Ionova, V.A., Russ. J. Org. Chem., 2011, vol. 47, p. 1715.
Yang, C., Li, J., Zhou, R., Chen, X., Gao, Y., and He, Z., Org. Biomol. Chem., 2015, vol. 13, p. 4869.
Wang, L., Li, S., Blümel, M., Philipps, A.R., Wang, A., Puttreddy, R., Rissanen, K., and Enders, D., Angew. Chem., Int. Ed., 2016, vol. 55, p. 11.110.
Chen, R., Xu, S., Fan, X., Li, H., Tang, Y., and He, Z., Org. Biomol. Chem., 2015, vol. 13, p. 398.
Sun, Q.-S., Lin, H., Sun, X., and Sun, X.-W., Tetrahedron Lett., 2016, vol. 57, p. 5673.
Vishwanath, M., Vinayagam, P., Gajulapalli, V.P.R., and Kesavan, V., Asian J. Org. Chem., 2016, vol. 5, p. 613.
Lv, H., Chen, X.-Y., Sun, L.-H., and Ye, S., J. Org. Chem., 2010, vol. 75, p. 6973.
Xie, Y., Que, Y., Li, T., Zhu, L., Yu, C., and Yao, C., Org. Biomol. Chem., 2015, vol. 13, p. 1829.
Yang, L., Wang, F., Chua, P.J., Lv, Y., Zhong, L.-J., and Zhong, G., Org. Lett., 2012, vol. 14, p. 2894.
Manoni, E. and Bandini, M., Eur. J. Org. Chem., 2016, p. 3135.
Wang, F., Li, Z., Wang, J., Li, X., and Cheng, J.-P., J. Org. Chem., 2015, vol. 80, p. 5279.
Liu, Y., Du, Y., Yu, A., Qin, D., and Meng, X., Tetrahedron, 2015, vol. 71, p. 7706.
Liu, Y., Du, Y., Yu, A., Mu, H., and Meng, X., Org. Biomol. Chem., 2016, vol. 14, p. 1226.
Rainoldi, G., Faltracco, M., Presti, L.L., Silvani, A., and Lesma, G., Chem. Commun., 2016, vol. 52, p. 11.575.
Xie, H., Yang, J.-X., Bora, P.P., and Kang, Q., Tetrahedron, 2016, vol. 72, p. 3014.
Reddy, R.S., Lagishetti, C., Kiran, I.N.C., You, H., and He, Y., Org. Lett., 2016, vol. 18, p. 3818.
Soderberg, B.C., Rector, S.R., and O’Neil, S.N., Tetrahedron Lett., 1999, vol. 40, p. 3657.
Ye, F. and Alper, H., J. Org. Chem., 2007, vol. 72, p. 3218.
Burns, B., Grigg, R., Sridharan, V., and Worakun, T., Tetrahedron Lett., 1988, vol. 29, p. 4325.
Zeng, R., Fu, C., and Ma, S., J. Am. Chem. Soc., 2012, vol. 134, p. 9597.
Zeng, R., Wu, S., Fu, C., and Ma, S., J. Am. Chem. Soc., 2013, vol. 135, p. 18.284.
Wang, H. and Glorius, F., Angew. Chem., Int. Ed., 2012, vol. 51, p. 7318.
Wang, H., Beiring, B., Yu, D.-G., Collins, K.D., and Glorius, F., Angew. Chem., Int. Ed., 2013, vol. 52, p. 12.430.
Thrimurtulu, N., Dey, A., Maiti, D., and Volla, C.M.R., Angew. Chem., Int. Ed., 2016, vol. 55, p. 12.361.
Harisha, A.S., Nayak, S.P., Nagarajan, K., Row, T.N.G., and Hosamani, A.A., Tetrahedron, 2016, vol. 72, p. 2880.
Elliott, I.W. and Takekoshi, Y., J. Heterocycl. Chem., 1976, vol. 13, p. 597.
Surikova, O.V. and Mikhailovskii, A.G., Russ. J. Org. Chem., 2015, vol. 51, p. 128.
Perevoshchikova, A.N., Gorbunov, A.A., Rozhkova, Yu.S., Slepukhin, P.A., and Shklyaev, Yu.V., Russ. J. Org. Chem., 2014, vol. 50, p. 513.
Chowdhury, C., Das, B., Mukherjee, S., and Achari, B., J. Org. Chem., 2012, vol. 77, p. 5108.
Wang, A.-F., Zhu, Y.-L., Wang, S.-L., Hao, W.-J., Li, G., Tu, S.-J., and Jiang, B., J. Org. Chem., 2016, vol. 81, p. 1099.
Xiao, Y.-C. and Moberg, C., Org. Lett., 2016, vol. 18, p. 308.
Ishikawa, T., Manabe, S., Aikawa, T., Kudo, T., and Saito, S., Org. Lett., 2004, vol. 6, p. 2361.
Qadir, M., Cobb, J., Sheldrake, P.W., Whittall, N., White, A.J.P., Hii, K.K., Horton, P.N., and Hursthouse, M.B., J. Org. Chem., 2005, vol. 70, p. 1545.
Tabata, H., Yoneda, T., Tasaka, T., Ito, S., Oshitari, T., Takahashi, H., and Natsugari, H., J. Org. Chem., 2016, vol. 81, p. 3136.
Cropper, E.L., White, A.J.P., Ford, A., and Hii, K.K., J. Org. Chem., 2006, vol. 71, p. 1732.
Peshkov, A.A., Peshkov, V.A., Pereshivko, O.P., and Van der Eycken, E.V., Tetrahedron, 2015, vol. 71, p. 3863.
Tietze, L.F. and Schimpf, R., Chem. Ber., 1994, vol. 127, p. 2235.
Kling, A., Backfisch, G., Delzer, J., Geneste, H., Graef, C., Holzenkamp, U., Hornberger, W., Lange, U.E.W., Lauterbach, A., Mack, H., Seitz, W., and Subkowski, T., Bioorg. Med. Chem. Lett., 2002, vol. 12, p. 441.
Viti, G., Giannotti, D., Altamura, M., Ricci, R., Volterra, G., Lecci, A., Borsini, F., and Pestellini, V., Eur J. Med. Chem., 1993, vol. 28, p. 439.
Majumbar, K.C., Chattopadyay, B., and Samanta, S., Tetrahedron Lett., 2009, vol. 50, p. 3178.
Gabriele, B., Salerno, G., Veltri, L., Costa, M., and Massera, C., Eur. J. Org. Chem., 2001, p. 4607.
Costa, M., Della Ca, N., Gabriele, B., Massera, C., Salerno, G., and Soliani, M., J. Org. Chem., 2004, vol. 69, p. 2469.
Bacchi, A., Glusoli, G.P., Costa, M., Sani, C., Gabriele, B., and Salerno, G., J. Organomet. Chem., 1998, vol. 562, p. 35.
Gabriele, B., Salerno, G., and Costa, M., Synlett, 2004, p. 2468.
Yoshida, M., Mizuguchi, T., and Shishido, K., Chem. Eur. J., 2012, vol. 18, p. 15.578.
Ishida, T., Kikuchi, S., Tsubo, T., and Yamada, T., Org. Lett., 2013, vol. 15, p. 848.
Saito, T., Ogawa, S., Takei, N., Kutsumura, N., and Otani, T., Org. Lett., 2011, vol. 13, p. 1098.
Vandavasi, J.K., Kuo, K.-K., Hu, W.-P., Shen, H.-C., Lo, W.-S., and Wang, J.-J., Org. Biomol. Chem., 2013, vol. 11, p. 6520.
Weyrauch, J.P., Hashmi, A.S.K., Schuster, A., Hengst, T., Schetter, S., Littmann, A., Rudolph, M., Hamzic, M., Visus, J., Rominger, F., Frey, W., and Bats, J.W., Chem. Eur. J., 2010, vol. 16, p. 956.
Brahma, K., Das, V., and Chowdhury, S., Tetrahedron, 2014, vol. 70, p. 5863.
Zhou, Y.-G., Yang, P.-Y., and Han, X.-W., J. Org. Chem., 2005, vol. 70, p. 1679.
Gazzola, S., Beccalli, E.M., Bernasconi, A., Borelli, T., Broggini, G., and Mazza, A., Eur. J. Org. Chem., 2016, p. 4534.
Liu, Z.-T., Wang, Y.-H., Zhu, F.-L., and Hu, X.-P., Org. Lett., 2016, vol. 18, p. 1190.
Mukovoz, P.P., Koz’minykh, V.O., Andreeva, V.A., Koz’minykh, E.N., and El’tsov, O.S., Russ. J. Org. Chem., 2015, vol. 51, p. 1453.
Zhang, D., Yang, Y., Gao, M., Shu, W., Wu, L., Zhu, Y., and Wu, A., Tetrahedron, 2013, vol. 69, p. 1849.
Makarenko, S.V., Kovalenko, K.S., Vershinina, Ya.S., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2014, vol. 50, p. 83.
Chegaev, K., Federico, A., Marini, E., Rolando, B., Fruttero, R., Morbin, M., Rossi, G., Fugnanesi, V., Bastone, A., Salmona, M., Badiola, N.B., Gasparini, L., Cocco, S., Ripoli, C., Grassi, C., and Gasco, A., Bioorg. Med. Chem., 2015, vol. 23, p. 4688.
Masaki, S., Kii, I., Sumida, Y., Kato-Sumida, T., Ogawa, Y., Ito, N., Nakamura, M., Sonamoto, R., Kataoka, N., Hosoya, T., and Hagiwara, M., Bioorg. Med. Chem., 2015, vol. 23, p. 4434.
Henry, C.E., Xu, Q., Fan, Y.C., Martin, T.J., Belding, L., Dudding, T., and Kwon, O., J. Am. Chem. Soc., 2014, vol. 136, p. 11.890.
Wang, C., Gao, Z., Zhou, L., Yuan, C., Sun, Z., Xiao, Y., and Guo, H., Org. Lett., 2016, vol. 18, p. 3418.
Conceição, D.S., Ferreira, D.P., Graça, V.C., Silva, C.R., Santos, P.F., and Vieira Ferreira, L.F., Tetrahedron, 2015, vol. 71, p. 967.
Xie, H., Liu, J.-C., and Ding, M.-W., Synthesis, 2016, vol. 48, p. 4541.
Buffat, M.G.P. and Thomas, E.J., Tetrahedron, 2016, vol. 72, p. 451.
Mancuso, R., Raut, D.S., Marino, N., De Luca, G., Giordano, C., Catalano, S., Barone, I., Andý, S., and Gabriele, B., Chem. Eur. J., 2016, vol. 22, p. 3053.
Reddy, A.S. and Swamy, K.C.K., Org. Lett., 2015, vol. 17, p. 2996.
Lee, S.-Y., Perotti, A., De Jonghe, S., Herdewijn, P., Hanck, T., and Müller, C.E., Bioorg. Med. Chem., 2016, vol. 24, p. 3157.
Mavrova, A.Ts., Yancheva, D., Anastassova, N., Anichina, K., Zvezdanovic, J., Djordjevic, A., Markovic, D., and Smelcerovic, A., Bioorg. Med. Chem., 2015, vol. 23, p. 6317.
Ramachary, D.B., Krishna, P.M., and Reddy, T.P., Org. Biomol. Chem., 2016, vol. 14, p. 6413.
Gvozdev, V.D., Shavrin, K.N., Egorov, M.P., and Nefedov, O.M., Mendeleev Commun., 2016, vol, 26, p. 3.
Pérez-Galán, P., Waldmann, H., and Kumar, K., Tetrahedron, 2016, vol. 72, p. 3647.
Ekebergh, A., Lingblom, C., Sandin, P., Wennerås, C., and Mårtensson, J., Org. Biomol. Chem., 2015, vol. 13, p. 3382.
McNulty, J., Keskar, K., Jenkins, H.A., Werstiuk, N.H., Bordón, C., Yolken, R., and Jones-Brando, L., Org. Biomol. Chem., 2015, vol. 13, p. 10.015.
Zhou, T., Wang, Y., Li, B., and Wang, B., Org. Lett., 2016, vol. 18, p. 5066.
Vachhani, D.D., Modha, S.G., Sharma, A., and Van der Eycken, E.V., Tetrahedron, 2013, vol. 69, p. 359.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © R.R. Gataullin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 1, pp. 7–49.
Rights and permissions
About this article
Cite this article
Gataullin, R.R. Exocyclic Double Bond in Benzo-Fused Nitrogen Heterocycles: Methods of Introduction and Syntheses with Its Participation. Russ J Org Chem 54, 1–44 (2018). https://doi.org/10.1134/S1070428018010013
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018010013