Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3215-3222.DOI: 10.6023/cjoc201904032 Previous Articles Next Articles
刘瑞婷a, 李振a, 王圣克a, 周锡庚ab*(
)
收稿日期:2019-04-12
发布日期:2019-07-03
通讯作者:
周锡庚
E-mail:xgzhou@fudan.edu.cn
基金资助:
Liu Ruitinga, Li Zhena, Wang Shengkea, Zhou Xigengab*()
Received:2019-04-12
Published:2019-07-03
Contact:
Zhou Xigeng
E-mail:xgzhou@fudan.edu.cn
Supported by:Share
Liu Ruiting, Li Zhen, Wang Shengke, Zhou Xigeng. Pd(OAc)2/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3215-3222.
| [1] |
(a) Stempel, E.; Gaich, T. Acc. Chem. Res. 2016, 49, 2390.
doi: 10.1021/acs.accounts.6b00265 |
|
(b) Sundberg, R. L. Indoles, Academic Press, London, 1996.
doi: 10.1021/acs.accounts.6b00265 |
|
|
(c) Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, Pergamon, Oxford, 2000.
doi: 10.1021/acs.accounts.6b00265 |
|
|
(d) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
doi: 10.1021/acs.accounts.6b00265 |
|
|
(e) Kochanowska-Karamyan, A. J.; Harmann, M. T. Chem. Rev. 2010, 110, 4489.
doi: 10.1021/acs.accounts.6b00265 |
|
|
(f) Shiri, M. Chem. Rev. 2012, 112, 3508.
doi: 10.1021/acs.accounts.6b00265 |
|
| [2] |
(a) Gao, S. S.; Li, X. M.; Williams, K.; Proksch, P.; Ji, N. Y.; Wang, B. G. J. Nat. Prod. 2016, 79, 2066.
doi: 10.1021/acs.jnatprod.6b00403 |
|
(b) Cheng, G. G.; Li, D.; Hou, B.; Li, X.-N.; Liu, L.; Chen, Y. Y.; Lunga, P. K.; Khan, A.; Liu, Y. P.; Zuo, Z. L.; Luo, X. D. J. Nat. Prod. 2016, 79, 2158.
doi: 10.1021/acs.jnatprod.6b00403 |
|
|
(c) Sim, D. S. Y.; Teoh, W. Y.; Sim, K. S.; Lim, S. H.; Thomas, N. F.; Low, Y. Y.; Kam, T. S. J. Nat. Prod. 2016, 79, 1048.
doi: 10.1021/acs.jnatprod.6b00403 |
|
|
(d) Wang, Z. R.; Hu, J. H.; Yang, X. P.; Feng, X.; Li, X. S.; Huang, L.; Chan, A. S. C. J. Med. Chem. 2018, 61, 1871.
doi: 10.1021/acs.jnatprod.6b00403 |
|
| [3] |
(a) Ragno, R.; Coluccia, A.; Regina, G. L.; Martino, G. D.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 3172.
doi: 10.1021/jm0512490 |
|
(b) Famiglini, V.; La Regina, G.; Coluccia, A.; Pelliccia, S.; Brancale, A.; Maga, G.; Crespan, E.; Badia, R.; Riveira-Muñoz, E.; Esté, J. A.; Ferretti, R.; Cirilli, R.; Zamperini, C.; Botta, M.; Schols, D.; Limongelli, V.; Agostino, B.; Novellino, E.; Silvestri R. J. Med. Chem. 2014, 57, 9945.
doi: 10.1021/jm0512490 |
|
|
(c) Famiglini, V.; La Regina, G.; Coluccia, A.; Masci, D.; Brancale, A.; Badia, R.; Riveira-Muñoz, E.; Esté, J. A. Crespan, E.; Brambilla, A.; Maga, G.; Catalano, M.; Limatola, C.; Formica, F. R.; Cirilli, R.; Novellino, E.; Silvestri, R. J. Med. Chem. 2017, 60, 6528.
doi: 10.1021/jm0512490 |
|
|
(d) Li, X; Gao, P.; Huang, B. S.; Zhou, Z. X.; Yu, Z.; Yuan, Z.; Liu, H. Q.; Pannecouque, C.; Daelemans, D.; De Clercq, E. Eur. J. Med. Chem. 2017, 126, 190.
doi: 10.1021/jm0512490 |
|
|
(e) Duchowicz1, P. R.; BaceloSilvina, D. E.; Fioressi, S. E.; Palermo, V.; Ibezim, N. E.; Romanelli, G. P. Med. Chem. Res. 2018, 27, 420.
doi: 10.1021/jm0512490 |
|
| [4] |
(a) Regina, G. L.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; Martino, G. D.; Matesanz, R.; Díaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.
doi: 10.1021/jm061479u |
|
(b) La Regina, G.; Bai, R.; Coluccia, A.; Famiglini, V.; Pelliccia, S.; Passacantilli, S.; Mazzoccoli, C.; Ruggieri, V.; Verrico, A.; Miele, A.; Monti, L.; Nalli, M.; Alfonsi, R.; Di Marcotullio, L.; Gulino, A.; Ricci, B.; Soriani, A.; Santoni, A.; Caraglia, M.; Porto, S.; Da Pozzo, E.; Martini, C.; Brancale, A.; Marinelli, L.; Novellino, E.; Vultaggio, S.; Varasi, M.; Mercurio, C.; Bigogno, C.; Dondio, G.; Hamel, E.; Lavia, P.; Silvestri, R. J. Med. Chem. 2015, 58, 5789.
doi: 10.1021/jm061479u |
|
|
(c) Sidhu, J. S.; Singla, R.; Mayank, Jaitak. V. Anti-Cancer Agents Med. Chem. 2016, 16, 160.
doi: 10.1021/jm061479u |
|
| [5] | Ramakrishna, V. S. N.; Shirsath, V. S.; Kambhampati, R. S.; Vishwakarma, S.; Kandikere, N. V.; Kota, S.; Jasti. V. WO 2007020653, 2007. |
| [6] |
Hu X.; Compton J. R.; AbdulHameed M. D. M.; Marchand C. L.; Robertson K. L.; Leary D. H.; Jadhav A.; Hershfield J. R.; Wallqvist A.; Friedlander A. M.; Legler P. M. J. Med. Chem. 2013, 56 5275.
doi: 10.1021/jm4001242 |
| [7] |
(a) Unangst, P. C.; Connor, D. T.; Stabler, S. R.; Weikert, R. J.; Carethers, M. E.; Kennedy, J. A.; Thueson, D. O.; Chestnut, J. C.; Adolphson, R. L.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360.
doi: 10.1021/jm00126a036 |
|
(b) Armer, R. E.; Wynne, G. M. WO 2008012511, 2008.
doi: 10.1021/jm00126a036 |
|
| [8] |
Nuth M.; Guan H.; Zhukovskaya N.; Saw Y. L.; Ricciardi R. P. J. Med. Chem. 2013, 56 3235.
doi: 10.1021/jm301735k |
| [9] |
(a) Hamel, P. J. Org. Chem. 2002, 67, 2854.
doi: 10.1021/jo0109220 |
|
(b) Vedejs, E.; Little, J. D. J. Org. Chem. 2004, 69, 1794.
doi: 10.1021/jo0109220 |
|
|
(c) Li, J. X.; An, Y. N.; Li, J. W.; Yang, S. R.; Wu, W. Q.; Jiang, H. F. Org. Chem. Front. 2017, 4, 1590.
doi: 10.1021/jo0109220 |
|
| [10] |
(a) Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. Eur. J. Org. Chem. 1998, 6, 1219.
doi: 10.1021/ol8021287 |
|
(b) Chen, Y.; Cho, C. H.; Larock, R. C. Org. Lett. 2009, 11, 173.
doi: 10.1021/ol8021287 |
|
|
(c) Guo, Y. J.; Tang, R. Y.; Li, J. H.; Zhong, P.; Zhang, X. G. Adv. Synth. Catal. 2009, 351, 2615.
doi: 10.1021/ol8021287 |
|
|
(d) Kumar, P. P.; Reddy, Y. D.; Reddy, C. V. R.; Devi, B. R.; Dubey, P. K. J. Sulfur Chem. 2014, 35, 356.
doi: 10.1021/ol8021287 |
|
|
(e) Yang, Y.; Zhang, S.; Tang, L.; Hu, Y. B.; Zha, Z. G.; Wang, Z. Y. Green Chem. 2016, 18, 2609.
doi: 10.1021/ol8021287 |
|
|
(f) Li, J.; Cai, Z. J.; Wang, S. Y.; Ji, S. J. Org. Biomol. Chem. 2016, 14, 9384.
doi: 10.1021/ol8021287 |
|
|
(g) Guo, W.; Tan, W.; Zhao, M. M.; Tao, K. L.; Zheng, L. Y.; Wu, Y. Q.; Chen, D. L.; Fan, X. L. RSC Adv. 2017, 7, 37739.
doi: 10.1021/ol8021287 |
|
|
(h) Liao, H. X.; Yang, Y.; Li, W. M.; Shen, C.; Zhang, P. F. Curr. Org. Chem. 2017, 21, 2509.
doi: 10.1021/ol8021287 |
|
|
(i) Šiaučiulis, M.; Sapmaz, S.; PulisA, P.; Procter, D. J. Chem. Sci. 2018, 9, 754.
doi: 10.1021/ol8021287 |
|
|
(j) Li, J. X.; Li, C. S.; Yang, S. R.; An, Y. N.; Wu, W. Q.; Jiang, H. F. J. Org. Chem. 2016, 81, 2875.
doi: 10.1021/ol8021287 |
|
|
(k) Lavekar, A. G.; Equbal, D.; Saima; Sinha, A. K. Adv. Synth. Catal. 2018, 360, 180.
doi: 10.1021/ol8021287 |
|
| [11] |
Li Z.; Hong L. C.; Liu R. T.; Shen J. Z.; Zhou X. G. Tetrahedron Lett. 2011, 52 1343.
doi: 10.1016/j.tetlet.2011.01.052 |
| [12] |
(a) Kumar, D. R.; Satyanarayana, G. Org. Lett. 2015, 17, 5894.
doi: 10.1021/acs.orglett.5b03077 |
|
(b) Liu, H.; Xi, F. G.; Sun, W.; Yang, N. N.; Gao, E. Q. Inorg. Chem. 2016, 55, 5753.
doi: 10.1021/acs.orglett.5b03077 |
|
|
(c) Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410.
doi: 10.1021/acs.orglett.5b03077 |
|
|
(d) Korvorapun, K.; Kaplaneris, N.; Rogge, T.; Warratz, S.; Stückl, A. C.; Ackermann, L. ACS Catal. 2018, 8, 886.
doi: 10.1021/acs.orglett.5b03077 |
|
| [13] |
(a) Fang, Y. Q.; Lautens, M. Org. Lett. 2005, 7, 3549.
doi: 10.1021/ol051286l |
|
(b) Fang, Y. Q.; Lautens, M. J. Org. Chem. 2008, 73, 538.
doi: 10.1021/ol051286l |
|
|
(c) Chai, D. I.; Lautens, M. J. Org. Chem. 2009, 74, 3054.
doi: 10.1021/ol051286l |
|
|
(d) Arthuis, M.; Pontikis, R.; Florent, J. C. Org. Lett. 2009, 11, 4608.
doi: 10.1021/ol051286l |
|
| [14] |
Li Z.; Hong J. Q.; Zhou X. G. Tetrahedron 2011, 67 3690.
doi: 10.1016/j.tet.2011.03.067 |
| [15] | CCDC 861518 for 4f contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/datarequest/cif. |
| [16] |
(a) Blanco, G. A.; Baumgartner, M. T. Tetrahedron Lett. 2011, 52, 7061.
doi: 10.1016/j.tetlet.2011.10.053 |
|
(b) Yan, G. b.; Borah, A. J.; Wang, L. G. Org. Biomol. Chem. 2014, 12, 9557.
doi: 10.1016/j.tetlet.2011.10.053 |
|
|
(c) Zhao, X.; Li, T. J.; Zhang, L. P.; Lu, K. Org. Biomol. Chem. 2016, 14, 1131.
doi: 10.1016/j.tetlet.2011.10.053 |
|
| [17] |
(a) Taniguchi, N. J. Org. Chem. 2006, 71, 7874.
doi: 10.1021/jo060834l |
|
(b) Stein, A.; Alves, D.; da Rocha, J.; Nogueira, C.; Zeni, G. Org. Lett. 2008, 10, 4983.
doi: 10.1021/jo060834l |
|
|
(c) Taniguchi, N. Tetrahedron 2009, 65, 2782.
doi: 10.1021/jo060834l |
|
|
(d) Wu, W.; Ding, Y. C.; Xie, P.; Tang, Q. J.; Pittman Jr. C. U.; Zhou, A. H. Tetrahedron 2017, 73, 2151.
doi: 10.1021/jo060834l |
|
| [18] |
(a) Ali, M. H.; McDermott, M. Tetrahedron Lett. 2002, 43, 6271.
doi: 10.1016/S0040-4039(02)01220-0 |
|
(b) Kabalka, G. W.; Reddy, M. S.; Yao, M. L. Tetrahedron Lett. 2009, 50, 7340.
doi: 10.1016/S0040-4039(02)01220-0 |
|
|
(c) Singh, D.; Deobald, A. M.; Camargo, L. S.; Tabarelli, G.; Rodrigues, O. D.; Braga, A. L. Org. Lett. 2010, 12, 3288.
doi: 10.1016/S0040-4039(02)01220-0 |
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