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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 11
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SYNTHETIC COMMUNICATIONS REVIEWS

C7-Friedel–Crafts alkylation of 4-aminoindoles with para-quinone methide derivatives under catalyst-free conditions

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Pages 1679-1686 | Received 18 Feb 2020, Published online: 24 Apr 2020

References

  • (a) Das, S. K.; Panda, G.; Chaturvedi, V.; Manju, Y. S.; Gaikwad, A. K.; Sinha, S. . Bioorg. Med. Chem. Lett. 2007, 17, 5586–5589. DOI: 10.1016/j.bmcl.2007.07.089. (b) Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289–292. DOI: 10.1016/j.bmcl.2007.10.083. (c) Al-Qawasmeh, R. A.; Lee, Y.; Cao, M. Y.; Gu, X. P.; Vassilakos, A.; Wright, J. A.; Young, A. Bioorg. Med. Chem. Lett. 2004, 14, 347–350. DOI: 10.1016/j.bmcl.2003.11.004. (d) Srivastava, A. K.; Sharma, R.; Mishra, R.; Balapure, A. K.; Murthy, P. S.; Panda, G. Bioorg. Med. Chem. 2006, 14, 1497. (e) Palchaudhuri, R.; Hergenrother, P. J. Bioorg. Med. Chem. Lett. 2008, 18, 5888–5891. DOI: 10.1016/j.bmcl.2008.07.128. (f) Palchaudhuri, R.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2008, 130, 10274–10281. DOI: 10.1021/ja8020999. (g) Risberg, K.; Guldvik, I. J.; Palchaudhuri, R.; Xi, Y. G.; Ju, J. F.; Fodstad, O.; Hergenrother, P. J.; Andersson, Y. J. J. Immunother. 2011, 34, 438–447. DOI: 10.1097/CJI.0b013e31821e00ae. (h) Kashyap, V. K.; Gupta, R. K.; Shrivastava, R.; Srivastava, B. S.; Srivastava, R.; Parai, M. K.; Singh, P.; Bera, S.; Panda, G. J. Antimicrob. Chemother. 2012, 67, 1188–1197. DOI: 10.1093/jac/dkr592. (i) Liu, X.; Luo, H. B.; Huang, Y. Y.; Bao, J. M.; Tang, G. H.; Chen, Y. Y.; Wang, J.; Yin, S. Org. Lett. 2014, 16, 282–285. DOI: 10.1021/ol403282f.
  • For recent reviews on p-QMs, see: (a) Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733–11764. DOI: 10.3390/molecules200711733. (b) Parra, A.; Tortosa, M. ChemCatChem 2015, 7, 1524–1526. DOI: 10.1002/cctc.201500176. (c) Chauhan, P.; Kaya, U.; Enders, D. Adv. Synth. Catal. 2017, 359, 888–912. DOI: 10.1002/adsc.201601342. (d) Li, W.; Xu, X.; Zhang, P.; Li, P. Chem. Asian J. 2018, 13, 2350–2359. DOI: 10.1002/asia.201800415.
  • For selected examples on cyclizations of p-QMs, see: (a) Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem. Int. Ed. 2016, 55, 12104–12108. DOI: 10.1002/anie.201606947. (b) Li, W.; Yuan, H.; Liu, Z.; Zhang, Z.; Cheng, Y.; Li, P. Adv. Synth. Catal. 2018, 360, 2460–2464. DOI: 10.1002/adsc.201800337. (c) Jiang, F.; Yuan, F.-R.; Jin, L.-W.; Mei, G.-J.; Shi, F. ACS Catal. 2018, 8, 10234–10240. DOI: 10.1021/acscatal.8b03410. (d) Sun, M.; Ma, C.; Zhou, S. ‐J.; Lou, S. ‐F.; Xiao, J.; Jiao, Y.; Shi, F. Angew. Chem. Int. Ed. 2019, 58, 8703–8708. DOI: 10.1002/anie.201901955. (e) Zhang, L.; Liu, Y.; Liu, K.; Liu, Z.; He, N.; Li, W. Biomol. Chem. 2017, 15, 8743–8747. DOI: 10.1039/C7OB02325A.
  • For selected examples on the 1,6-addition of p-QMs, see: (a) Lin, C.; Shen, Y.; Huang, B.; Liu, Y.; Cui, S. J. Org. Chem. 2017, 82, 3950–3956. DOI: 10.1021/acs.joc.7b00145. (b) Xie, K. X.; Zhang, Z. P.; Li, X. Org. Lett. 2017, 19, 6708–6711. DOI: 10.1021/acs.orglett.7b03433. (c) Roy, D.; Panda, G. Synthesis 2019, 51, 4434.(d) Kale, S. B.; Jori, P. K.; Thatikonda, T.; Gonnade, R. G.; Das, U. Org. Lett. 2019, 21, 7736–7740. DOI: 10.1021/acs.orglett.9b02641. (e) Shirsath, S. R.; Shinde, G. H.; Shaikh, A. C.; Muthukrishnan, M. J. Org. Chem. 2018, 83, 12305–12314. DOI: 10.1021/acs.joc.8b01926. (f) Vaishanv, N. K.; Gupta, A. K.; Kant, R.; Mohanan, K. J. Org. Chem. 2018, 83, 8759–8767. DOI: 10.1021/acs.joc.8b01074. (g) Jiang, X. L.; Wu, S. F.; Wang, J. R.; Mei, G. J.; Shi, F. Adv. Synth. Catal. 2018, 360, 4225–4235. DOI: 10.1002/adsc.201800829. (h) Dong, N.; Zhang, Z. P.; Xue, X. S.; Li, X.; Cheng, J. P. Angew. Chem. Int. Ed. 2016, 55, 1460–1464. DOI: 10.1002/anie.201509110. (i) Zhang, X. Z.; Gan, K. J.; Liu, X. X.; Deng, Y. H.; Wang, F. X.; Yu, K. Y.; Zhang, J.; Fan, C. A. Org. Lett. 2017, 19, 3207–3210. DOI: 10.1021/acs.orglett.7b01331.
  • For examples on the synthesis of triarylmethanes using p-QMs, see: (a) Wang, J. R.; Jiang, X. L.; Hang, Q. Q.; Zhang, S.; Mei, G. J.; Shi, F. J. Org. Chem. 2019, 84, 7829–7839. DOI: 10.1021/acs.joc.9b00710. (b) Goswami, P.; Anand, R. V. ChemistrySelect 2016, 1, 2556. DOI: 10.1002/slct.201600553. (c) Wang, Z.; Wong, Y. F.; Sun, J. Angew. Chem. Int. Ed. 2015, 54, 13711–13714. DOI: 10.1002/anie.201506701. (d) Gao, S.; Xu, X.; Yuan, Z.; Zhou, H.; Yao, H.; Lin, A. Eur. J. Org. Chem. 2016, 2016, 3006–3012. DOI: 10.1002/ejoc.201600385. (e) Cheng, Y.; Fang, Z.; Jia, Y.; Lu, Z.; Li, W.; Li, P. RSC Adv. 2019, 9, 24212–24217. DOI: 10.1039/C9RA04768A. (f) Wong, Y. F.; Wang, Z.; Sun, J. Org. Biomol. Chem. 2016, 14, 5751–5754. DOI: 10.1039/C6OB00125D. (g) Zhou, T.; Li, S.; Huang, B.; Li, C.; Zhao, Y.; Chen, J.; Chen, A.; Xiao, Y.; Liu, L.; Zhang, J. Org. Biomol. Chem. 2017, 15, 4941–4945. DOI: 10.1039/C7OB00911A. (h) Mei, G. J.; Xu, S. L.; Zheng, W. Q.; Bian, C. Y.; Shi, F. J. Org. Chem. 2018, 83, 1414–1421. DOI: 10.1021/acs.joc.7b02942. (i). Huang, G. B.; Huang, W. H.; Guo, J.; Xu, D. L.; Qu, X. C.; Zhai, P. H.; Zheng, X. H.; Weng, J.; Lu, G. Adv. Synth. Catal. 2019, 361, 1241–1246. DOI: 10.1002/adsc.201801446.
  • (a) Sundberg, R. J. In The Chemistry of Indoles; Academic Press: New York, 1970. (b) Brown, R. K. In Indoles; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972. (c) Sundberg, R. J. In Indoles; Academic Press: Sunderland, 1996. (d) Chen, J.-B.; Jia, Y.-X. Org. Biomol. Chem. 2017, 15, 3550–3567. DOI: 10.1039/C7OB00413C. (e) Zhang, Y.-C.; Jiang, F.; Shi, F. Acc. Chem. Res. 2020, 53, 425–446.
  • (a) Poulsen, P. H.; Feu, K. S.; Paz, B. M.; Jensen, F.; Jørgensen, K. A. Angew. Chem. 2015, 127, 8321; Angew. Chem. Int. Ed. 2015, 54, 8203. DOI: 10.1002/ange.201503370. (b) Montesinos-Magraner, M.; Vila, C.; Rendón-Patiño, A.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. ACS Catal. 2016, 6, 2689–2693. DOI: 10.1021/acscatal.6b00260. (c) Montesinos-Magraner, M.; Vila, C.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. Org. Lett. 2017, 19, 1546–1549. DOI: 10.1021/acs.orglett.7b00354. (d) Xiao, M. J.; Xu, D. F.; Liang, W. H.; Wu, W. Y.; Chan, A. S. C.; Zhao, J. L. Adv. Synth. Catal. 2018, 360, 917–924. DOI: 10.1002/adsc.201701089. (e) Yang, Z. T.; Yang, W. L.; Chen, L.; Sun, H.; Deng, W. P. Adv. Synth. Catal. 2018, 360, 2049–2054. DOI: 10.1002/adsc.201800181. (f) Liu, J. Y.; Yang, X. C.; Lu, H.; Gu, Y. C.; Xu, P. F. Org. Lett. 2018, 20, 2190–2194. DOI: 10.1021/acs.orglett.8b00503. (g) Vila, C.; Rostoll-Berenguer, J.; Sánchez-García, R.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. J. Org. Chem. 2018, 83, 6397–6407. DOI: 10.1021/acs.joc.8b00612.
  • (a) Xun, W.; Xu, B.; Chen, B.; Meng, S. S.; Chan, A. S. C.; Qiu, F. G.; Zhao, J. L. Org. Lett. 2018, 20, 590–593. DOI: 10.1021/acs.orglett.7b03703. (b) Cai, L.; Zhao, Y. L.; Huang, T. K.; Meng, S. S.; Jia, X.; Chan, A. S. C.; Zhao, J. L. Org. Lett. 2019, 21, 3538–3542. DOI: 10.1021/acs.orglett.9b00821. (c) Huang, T. K.; Zhao, Y. L.; Meng, S. S.; Chan, A. S. C.; Zhao, J. L. Adv. Synth. Catal. 2019, 361, 3632–3638. DOI: 10.1002/adsc.201900377. (d) Zhao, Y. L.; Cai, L.; Huang, T. K.; Meng, S. S.; Chan, A. S. C.; Zhao, J. L. Adv. Synth. Catal. 2020, 362, 1309–1316. DOI: 10.1002/adsc.201901380.

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