Progress in the Synthesis of 2,3-Disubstituted Indole by Cyclization

doi:10.6023/cjoc201605024

Abstract

In recent years, there are many reports about the synthesis of 2,3-disubstituted indole by cyclization. Most of these approaches are catalyzed by different transition metals and metal-free catalysis conditions using phenylnydrazines, anilines and nitrobenzenes as main substrates. These methods have been a powerful strategy to obtain 2,3-disubstituted indoles. The recent progress of the synthesis of 2,3-disubstituted indoles by cyclization with the different substrates systems is summarized.

Key words: 2,3-disubstituted indole, synthesis, heterocyclic compound, cyclization

Cite this article

Liang Ting, Li Jun, Liu Yu, Wu Caixia, Wang Jing, Lan Jinping, Liu Kai-yang. Progress in the Synthesis of 2,3-Disubstituted Indole by Cyclization[J]. Chin. J. Org. Chem., 2016, 36(11): 2619-2633.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Fischer, E.; Jourdan, F. Ber. 1883, 16, 2241.
[2] Malleron, J. L.; Gueremy, C.; Mignani, S.; Peyronel, J. F.; Truchon, A.; Blanchard, J. C.; Doble, A.; Laduron, P.; Piot, O. J. Med. Chem. 1993, 36, 1194.
[3] Yutaka, A.; Toshihiko, M.; Akihiro, O. Tetrahedron Lett. 1996, 37, 9203.
[4] Nicolaou, K. C.; Lee, S. H.; Estrada, A. A.; Zak, M. Angew. Chem., Int. Ed. 2005, 44, 3736.
[5] Narkowicz, C. K.; Blackman, A. J.; Lacey, E.; Gill, J. H.; Hei-land, K. J. Nat. Prod. 2002, 65, 938.
[6] Ren, J.-Q.; Fan, H.-D. Chin. J. Hosp. Pharm. 1993, 13, 492 (in Chinese). (任进民, 樊德厚, 中国医院药学杂志, 1993, 13, 492.)
[7] Hughes, D. L.; Zhao, D. J. Org. Chem. 1993, 58, 228.
[8] Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
[9] Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324.
[10] Liu, K.-G.; Robichaud, A. J.; Lo, J. R.; Mattes, J. F.; Cai, Y.-X.; Org. Lett. 2006, 8, 5769.
[11] Dykstra, K. D.; Guo, L.-Q.; Birzin, E. T.; Chan, W.-D.; Yang, Y.-T.; Hayes, E. C.; DaSilva, C. A.; Pai, L. Y.; Mosley, R. T.; Kraker, B.; Fitzgerald, P. M. D.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. Bioorg. Med. Chem. Lett. 2007, 17, 2322.
[12] Xu, D.-Q.; Yang, W.-L.; Luo, S.-P.; Wang, B.-T.; Wu,-J.; Xu, Z. -Y. Eur. J. Org. Chem. 2007, 1007.
[13] Muzalevskiy, V. M.; Nenajdenko, V. G.; Shastin, A. V.; Balenkova, E. S.; Haufe, G. Tetrahedron 2009, 65, 7553.
[14] Patil, N. T.; Konala, A. Eur. J. Org. Chem. 2010, 6831.
[15] Li, B.-L.; Xu, D.-Q.; Zhong, A.-G. J. Flurine Chem. 2012, 144, 45.
[16] Siddalingamurthy, E.; Mahadevan, K. M.; Masagalli, J. N.; Ha-rishkumar, H. N. Tetrahedron Lett. 2013, 54, 5591.
[17] Laube, M.; Tondera, C.; Sharma, S. K.; Bechmann, N.; Pietzsch, F. J.; Pigorsch, A.; Koeckerling, M.; Wuest, F.; Pietzsch, J.; Kniess, T. RSC Adv. 2014, 4, 38726.
[18] Gore, S.; Baskaran, S.; König, B. Org. Lett. 2012, 14, 4568.
[19] Zhang, H.; Hu, R.-B.; Liu, N.; Li, S.-X. Yang, S.-D. Org. Lett. 2016, 18, 28.
[20] Pews-Davtyan, A.; Tillack, A.; Schmoele, A. C.; Ortinau, S.; Frech, M. J.; Rolfs, A.; Beller, M. Org. Biomol. Chem. 2010, 8, 1149.
[21] Pews-Davtyan, A.; Beller, M. Org. Biomol. Chem. 2011, 9, 6331.
[22] Gehrmann, T.; Lloret, F. J.; Scholl, S. A.; Wadepohl, H.; Gade, L. H. Angew. Chem., Int. Ed. 2011, 50, 5757.
[23] Gehrmann, T.; Scholl, S. A.; Fillol, J. L.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2012, 18, 3925.
[24] Matsuda, T.; Tomaru, Y. Tetrahedron Lett. 2014, 55, 3302.
[25] Zhou, B.; Du, J.-J.; Yang, Y.-X.; Li, Y.-C. Chem. Eur. J. 2014, 20, 12768.
[26] Zhang, Z.-X; Jiang, H.; Huang, Y. Org. Lett. 2014, 16, 5976.
[27] Fan, Z.-L.; Song, S.-S.; Li, W.; Geng, K.-J.; Xu, Y.-J.; Miao, Z.-H.; Zhang, A. Org. Lett. 2015, 17, 310.
[28] Moballigh, A.; Ralf, J.; Majeed, S. A.; Holger, K.; Matthias, B. Tetrahedron Lett. 2004, 45, 869.
[29] Khedkar, V.; Tillack, A.; Michalik, M.; Beller, M. Tetrahedron Lett. 2004, 45, 3123.
[30] Li, D.-Y.; Chen, H.-J.; Liu, P.-N. Org. Lett. 2014, 16, 6176.
[31] Jiang, J.-Z.; Wang, Y. Chin. J. Org. Chem. 2006, 26, 1025 (in Chinese). (蒋金芝, 王艳, 有机化学, 2006, 26, 1025.)
[32] Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159.
[33] Mun, H. S.; Ham, W. H.; Jeong, J. H. J. Comb. Chem. 2005, 7, 130.
[34] Tsuji, Y.; Huh, K. T.; Watanabe, Y. Tetrahedron Lett. 1986, 27, 377.
[35] Tursky, M.; Lorentz-Petersen, Linda L. R.; Olsen, L. B.; Madsen, R. Org. Biomol. Chem. 2010, 8, 5576.
[36] Zhang, M.; Xie, F.; Wang, X.-T.; Yan, F.-X.; Wang, T.; Chen, M.-M.; Ding, Y.-Q. RSC Adv. 2013, 3, 6022.
[37] Pena-Lopez, M.; Neumann, H.; Beller, M. Chem. Eur. J. 2014, 20, 1818.
[38] Tokunaga, M.; Ota, M.; Haga, M. A; Wakatsuki, Y. Tetrahedron Lett. 2001, 42, 3865.
[39] Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2006, 71, 4951.
[40] Huestis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338.
[41] Kathiravana, S.; Nicholls, I. A. Chem. Commun. 2014, 50, 14964.
[42] Sagadevan, A.; Ragupathi, A.; Hwang, K. C. Angew. Chem., Int. Ed. 2015, 54, 13896.
[43] Reddy, P. V.; Annapurna, M.; Srinivas, P.; Likhar, P. R.; Kantam, M. L. New J. Chem. 2015, 39, 3399.
[44] Sharma, S.; Pathare, R. S.; Maurya, A. K.; Gopal, K.; Roy, T. K.; Sawant, D. M.; Pardasani, R. T. Org. Lett. 2016, 18, 356.
[45] Bard, R. R.; Bunnett, J. F. J. Org. Chem. 1980, 45, 1546.
[46] Suzuki, H.; Thiruvikraman, S. V.; Osuka, A. Synthesis 1984, 616.
[47] Chen, C.-Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676.
[48] Na?aré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526.
[49] Liu, X.-G.; Li, Z.-H.; Xie, J.-W.; Liu, P.; Zhang, J.; Dai, B. Tetrahedron. 2016, 72, 653.
[50] Wensbo, D.; Eriksson, A.; Jeschke, T.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 2823.
[51] Jeschke; W.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 6471.
[52] Witulski, B.; Alayrac, C.; TevzadzeSaeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
[53] Lu, B. Z.; Wei, H.-X.; Zhang, Y.-D.; Zhao, W.-Y.; Dufour, M.; Li, G.-S.; Farina, V.; Senanayake, C. H. J. Org. Chem. 2013, 78, 4558.
[54] Hao, W.; Geng, W.-Z; Zhang, W.-X; Xi, Z.-F. Chem. Eur. J. 2014, 20, 2605.
[55] Johnson, F.; Subramanian, R. J. Org. Chem. 1986, 51, 5040.
[56] Cui, S.-L.; Wang, J.; Wang, Y.-G. J. Am. Chem. Soc. 2008, 130, 13526.
[57] Saito, A.; Oda, S.; Fukaya, H.; Hanzawa, Y. J. Org. Chem. 2009, 74, 1517.
[58] Hayashi, S.; Ueno, N.; Murase, A.; Nakagawa, Y.; Takada, J. Eur. J. Med. Chem. 2012, 50, 179.
[59] Deng, G.-B.; Zhang, J.-L.; Liu, Y.-Y.; Liu, B.; Yang, X.-H.; Li, J.-H. Chem. Commun. 2015, 51, 1886.
[60] Nicolaou, K. C.; Lee, S. H.; Estrada, A. A.; Zak, M. Angew. Chem., Int. Ed. 2005, 44, 3736.
[61] Nicolaou, K. C.; Estrada, A. A.; Lee, S. H.; Freestone, G. C. Angew. Chem., Int. Ed. 2006, 45, 5364.
[62] Ragaini, F.; Rapetti, A.; Visentin, E.; Monzani, M.; Caselli, A.; Cenini, S. J. Org. Chem. 2006, 71, 3748.
[63] Penoni, A.; Nicholas, K. M. Chem. Commun. 2002, 484.
[64] Wylie, L.; Innocenti, P.; Whelligan, D. K.; Hoelder, S. Org. Biomol. Chem. 2012, 10, 4441.
[65] Coffman, K. C.; Palazzo, T. A.; Hartley, T. P.; Fettinger, J. C.; Tantillo, D. J.; Kurth, M. J. Org. Lett. 2013, 15, 2062.
[66] Zhou, F.; Wang, D.-S.; Driver, T. G. Adv. Synth. Catal. 2015, 357, 3463.
[67] Penoni, A.; Volkmann, J.; Nicholas, K. M. Org. Lett. 2002, 4, 699.
[68] Murru, S.; Gallo, A. A.; Srivastava, R. S. Eur. J. Org. Chem. 2011, 2035.
[69] Yan, H.; Wang, H.-L.; Li, X.-C.; Xin, X.-Y.; Wang, C.-X.; Wan, B.-S. Angew. Chem., Int. Ed. 2015, 54, 10613.
[70] Zhou, Z.; Liu, G.-X.; Chen, Y.; Lu, X.-Y. Adv. Synth. Catal. 2015, 357, 2944.
[71] Sharma, P.; Liu, R.-S. Org. Lett. 2016, 18, 412.
[72] (a) Ross, R. A.; Brockie, H. C.; Stevenson, L. A.; Murphy, V. L.; Templeton, F.; Makriyannis, A.; Pertwee, R. G. Br. J. Pharmacol. 1999, 126, 665.
(b) Dutta, A. K.; Ryan, W.; Thomas, B. F.; Singer, M.; Compton, D. R.; Martin, B. R.; Razdan, R. K. Bioorg. Med. Chem. 1997, 5, 1591.
(c) Murataeva, N.; Mackie, K.; Straiker, A. Pharmacol. Res. 2, 66, 437.
[73] Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213.
[74] Onitsuka, K.; Suzuki, S.; Takahashi, S. Tetrahedron Lett. 2002, 43, 6197.
[75] Tobisu, M.; Fujihara, H.; Koh, K.; Chatani, N. J. Org. Chem. 2010, 75, 4841.
[76] Nanjo, T.; Yamamoto, S.; Tsukano, C.; Takemoto, Y. Org. Lett. 2013, 15, 3754.
[77] Zhang, B.; Studer, A. Org. Lett. 2014, 16, 1216.
[78] Wetzel, A.; Gagos?, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
[79] Lu, B.; Luo, Y.-D.; Liu, L.-Z.; Ye, L.-W.; Wang, Y.-Z.; Zhang, L.-M. Angew. Chem., Int. Ed. 2011, 50, 8358.
[80] Kong, C.; Jana, N.; Driver, T. G. Org. Lett. 2013, 15, 824.
[81] Abaev, V. T.; Plieva, A. T.; Chalikidi, P. N.; Uchuskin, M. G.; Trushkov, I. V.; Butin, A. V. Org. Lett. 2014, 16, 4150.
[82] Phillips, R. M.; Hendriks, H. R.; Peters, G. J. Br. J. Pharmacol. 2013, 168, 11.
[83] (a) Asberg, A.; Holdaas, H. Expert Rev. Cardiovasc. Ther. 2004, 2, 641.
(b) Zacharia, J. T.; Tanaka, T.; Hayashi, M. J. Org. Chem. 2010, 75, 7514.
[84] Chen, K.; Zhu, Z.-Z.; Liu, J.-X.; Tang, X.-Y.; Wei, Y.; Shi, M. Chem. Commun. 2015, 52, 350.
[85] Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
[86] Haag, B. A.; Zhang, Z.-G.; Li, J.-S.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 9513.
[87] Wang, H.-B.; Mudraboyina, B. P.; Wisner, J. A. Chem. Eur. J. 2012, 18, 1322.
[88] Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 11960.
[89] Dawande, S. G.; Kanchupalli, V.; Kalepu, J.; Chennamsetti, H.; Lad, B. S.; Katukojvala, S. Angew. Chem., Int. Ed. 2014, 53, 4076.
[90] Martins, G. M.; Zeni, G.; Back, D. F.; Kaufman, T. S.; Silveira, C. C. Adv. Synth. Catal. 2015, 357, 3255.
[91] (a) Tanaka, M.; Li, X.; Hikawa, H.; Suzuki, T.; Tsutsumi, K.; Sato, M.; Takikawa, O.; Suzuki, H.; Yokoyama, Y. Bioorg. Med. Chem. 2013, 21, 1159.
(b) Chand, P.; Chesney, J. A.; Clem, B. F.; Tapolsky, G. H.; Tel-ang, S.; Trent, J. O. WO 2011/103557, 2011[Chem. Abstr. 2011, 155, 371778].
(c) Kai, M.; Noda, A.; Noda, H.; Goto, S. Chem. Pharm. Bull. 1988, 36, 3604.
[92] (a) Neo, A. G.; Lypez, C.; Lypez, A.; Castedo, L.; Tojo, G. Tetrahedron 2013, 69, 11010.
(b) Tietze, L.; von Hof, J. M. WO 2011/054837, 2011[Chem. Abstr. 2011, 154, 565441].
(c) Jones, G. B.; Mathews, J. E. Tetrahedron. 1997, 53, 14599.
[93] Nakamura, L.; Nemoto, T.; Shiraiwa, N.; Terada, M. Org. Lett. 2009, 11, 1055.
[94] Cai, Q.; Li, Z.-Q.; Wei, J.-J; Ha, C.-Y.; Pei, D.-Q.; Ding, K. Chem. Commun. 2009, 7581.
[95] Zhang, Y.-H.; Liu, S.; Yu, W.-W.; Hu, M.; Zhang, G.-L.; Yu, Y.-P. Tetrahedron 2013, 69. 2070.
[96] Goriya, Y.; Ramana, C. V. Chem. Commun. 2014, 50, 7790.
[97] Novikov, M. S.; Khlebnikov, A. F.; Rostovskii, N. V.; Tcyrulnikov, S.; Suhanova, A. A.; Zavyalov, K. V.; Yufit, D. S. J. Org. Chem. 2015, 80, 18.

环化反应合成2,3-二取代吲哚的研究进展