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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Preparation of Tetrasubstituted Bis(3-indolyl)methanes from Indoles and Acetophenes Using 1,3-dibromo-5,5-dimehtylhydantoin as an Efficient Catalyst

Author(s): Zubiao Zheng, Daoxin Zha, Peng Cui, Caixia Ye, Lei Jin and Bingbing Han*

Volume 19, Issue 10, 2022

Published on: 16 February, 2022

Page: [850 - 856] Pages: 7

DOI: 10.2174/1570178619666220111122536

Price: $65

Abstract

A new process that could efficiently prepare tetrasubstituted bis(3-indolyl)methanes from various indoles and acetophenones with 1,3-Dibromo-5,5-dimehtylhydantoin(DBDMH) as a catalyst was reported. The effects of catalysts, solvents, and reaction temperature were investigated. Under the optimal condition, most of the tetrasubstituted bis(3-indolyl)methanes were obtained in 90–99% yields.

Keywords: Tetrasubstituted BIMs, indoles, acetophenones, DBDMH, catalyst, bisindolylation.

Graphical Abstract

[1]
Merinos, J.P.G.; Ruíz, H.L.; López, Y.; Lima, S.R. Lett. Org. Chem., 2015, 12(5), 332-336.
[http://dx.doi.org/10.2174/1570178612666150220225335] [PMID: 26120289]
[2]
Taylor, R.D.; MacCoss, M.; Lawson, A.D.J. J. Med. Chem., 2014, 57(14), 5845-5859.
[http://dx.doi.org/10.1021/jm4017625] [PMID: 24471928]
[3]
Kaushik, N.K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C.H.; Verma, A.K.; Choi, E.H. Molecules, 2013, 18(6), 6620-6662.
[http://dx.doi.org/10.3390/molecules18066620] [PMID: 23743888]
[4]
Zeligs, M. J. Med. Food, 1998, 1, 67-82.
[http://dx.doi.org/10.1089/jmf.1998.1.67]
[5]
Grubbs, C.J.; Steele, V.E.; Casebolt, T.; Juliana, M.M.; Eto, I.; Whitaker, L.M.; Dragnev, K.H.; Kelloff, G.J.; Lubet, R.L. Anticancer Res., 1995, 15(3), 709-716.
[PMID: 7645947]
[6]
Benabadji, S.H.; Wen, R.; Zheng, J.B.; Dong, X.C.; Yuan, S.G. Acta Pharmacol. Sin., 2004, 25(5), 666-671.
[PMID: 15132835]
[7]
Garbe, T.R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M. Yukawa. J. Nat. Prod., 2000, 63, 596-598.
[http://dx.doi.org/10.1021/np990517s] [PMID: 10843566]
[8]
Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod., 1995, 58, 1254-1260.
[http://dx.doi.org/10.1021/np50122a017] [PMID: 7595591]
[9]
Zhang, D.; Du, K.; Zhao, Y.; Shi, S.; Wu, Y.; Jia, Q.; Chen, K.; Li, Y.; Wang, R. Nat. Prod. Res., 2021, 35(2), 244-250.
[http://dx.doi.org/10.1080/14786419.2019.1624960] [PMID: 31174427]
[10]
Nagre, D.T.; Mali, S.N.; Thorat, B.R.; Thorat, S.A.; Chopade, A.R.; Farooqui, M.; Argawal, B. Curr. Enzym. Inhib., 2021, 17, 1-17.
[http://dx.doi.org/10.2174/157340801701210125153248]
[11]
Singh, A.; Kaur, G.; Baetjee, B. Curr. Org. Chem., 2020, 24, 583-621.
[http://dx.doi.org/10.2174/1385272824666200228092752]
[12]
Swetha, A. MadhuBabu, B.; Meshram, H.M. Tetrahedron Lett., 2015, 56, 1775-1779.
[http://dx.doi.org/10.1016/j.tetlet.2015.02.032]
[13]
Mahboobi, S.; Uecker, A.; Sellmer, A.; Cénac, C.; Höcher, H.; Pongratz, H.; Eichhorn, E.; Hufsky, H.; Trümpler, A.; Sicker, M.; Heidel, F.; Fischer, T.; Stocking, C.; Elz, S.; Böhmer, F.D.; Dove, S. J. Med. Chem., 2006, 49(11), 3101-3115.
[http://dx.doi.org/10.1021/jm058033i] [PMID: 16722630]
[14]
Grosso, C.; Cardoso, A.L.; Lemos, A.; Varela, J.; Rodrigues, M.J.; Custodio, L.; Barreira, L.; Melo, T. Eur. J. Med. Chem., 2015, 93, 9-15.
[http://dx.doi.org/10.1016/j.ejmech.2015.01.050] [PMID: 25644672]
[15]
Rahimi, M.; Huang, K.L.; Tang, C.K. Cancer Lett., 2010, 295, 59-68.
[http://dx.doi.org/10.1016/j.canlet.2010.02.014] [PMID: 20299148]
[16]
Sashidhara, K.V.; Kumar, A.; Kumar, M.; Srivastava, A.; Puri, A. Bioorg. Med. Chem. Lett., 2010, 20, 6504-6507.
[http://dx.doi.org/10.1016/j.bmcl.2010.09.055] [PMID: 20932744]
[17]
Sashidhara, K.V.; Modukuri, R.K.; Sonkar, R.; Rao, K.B.; Bhatia, G. Eur. J. Med. Chem., 2013, 68, 38-46.
[http://dx.doi.org/10.1016/j.ejmech.2013.07.009] [PMID: 23954239]
[18]
Bharate, S.B.; Bharate, J.B.; Khan, S.I.; Tekwani, B.L.; Jacob, M.R.; Mudududdla, R.; Yadav, R.R.; Singh, B.; Sharma, P.R.; Maity, S.; Singh, B.; Khan, I.A.; Vishwakarma, R.A. Eur. J. Med. Chem., 2013, 63, 435-443.
[http://dx.doi.org/10.1016/j.ejmech.2013.02.024] [PMID: 23517732]
[19]
Sarva, S.; Harinath, J.S.; Sthanikam, S.P.; Ethiraj, S.; Vaithiyalingam, M.; Cirandur, S.R. Chin. Chem. Lett., 2016, 27, 16-20.
[http://dx.doi.org/10.1016/j.cclet.2015.08.012]
[20]
Lo, K.K.W.; Tsang, K.H.K.; Hui, W.K.; Zhu, N. Chem. Commum., 2003, 2704-2705.
[http://dx.doi.org/10.1039/B306914A] [PMID: 14649820]
[21]
Wu, Z.Q.; Wang, G.; Li, Z.L.; Feng, E.K.; Liang, Y.P.; Zhan, H.J. Synth. Commun., 2021, 51, 1206-1217.
[22]
Ghafuri, H.; Ghorbani, B.; Zand, H.R.E. Lett. Org. Chem., 2018, 15, 295-301.
[http://dx.doi.org/10.2174/1570178614666170707151649]
[23]
Li, M.X.; Pu, X.J.; Zhang, X.; Zheng, Z.; Gao, H.; Xiao, W.L.; Wan, C.P.; Mao, Z.W. Curr. Org. Synth., 2020, 17, 144-150.
[http://dx.doi.org/10.2174/1570179417666200124103400] [PMID: 31976840]
[24]
Kaur, G.; Kumar, R.; Saroch, S.; Gupta, V.K.; Banerjee, B. Curr. Organocatal., 2021, 8, 147-159.
[http://dx.doi.org/10.2174/2213337207999200713145440]
[25]
Firouzabadi, H.; Iranpoor, N.; Jafari, A.A. J. Mol. Catal. Chem., 2006, 244, 168-172.
[http://dx.doi.org/10.1016/j.molcata.2005.09.005]
[26]
Khaligh, N.G.; Mihankhah, T.; Johan, M.R.; Ching, J.J. J. Mol. Liq., 2018, 259, 260-273.
[http://dx.doi.org/10.1016/j.molliq.2018.03.044]
[27]
Honarmand, M.; Esmaeili, E. J. Mol. Liq., 2017, 225, 741-749.
[http://dx.doi.org/10.1016/j.molliq.2016.10.136]
[28]
Shaikh, S.I.; Zaheer, Z.; Mokale, S.N. Lett. Org. Chem., 2018, 15, 32-38.
[29]
Rivas-Loaiza, J.A.; Reyes-Escobedo, C.E.; Lopez, Y.; Rojas-Lima, S.; García-Merinos, J.P.; López-Ruiz, H. Lett. Org. Chem., 2019, 16, 959-968.
[http://dx.doi.org/10.2174/1570178616666190222150915]
[30]
Nemallapudi, B.R.; Zyryanov, G.V.; Avula, B.; Guda, M.R.; Cirandur, S.R.; Venkataramaiah, C.; Rajendra, W.; Gundala, S. Bioorg. Chem., 2019, 87, 465-473.
[http://dx.doi.org/10.1016/j.bioorg.2019.03.005] [PMID: 30927587]
[31]
Tabrizi, A.K.; Khademieslam, H.; Hemmasi, A.H.; Bazyar, B.; Atghia, S.V. Green Chem. Lett. Rev., 2020, 13, 328-340.
[http://dx.doi.org/10.1080/17518253.2020.1839571]
[32]
Mhaldar, S.N.; Mandrekar, K.S.; Gawde, M.K.; Shet, R.V.; Tilve, S.G. Synth. Commun., 2019, 49, 94-101.
[http://dx.doi.org/10.1080/00397911.2018.1542732]
[33]
Indurthi, H.K.; Virdi, R.; Koli, P.; Rao, D.N.; Sharma, D.K. Synth. Commun., 2021, 51, 139-150.
[http://dx.doi.org/10.1080/00397911.2020.1849724]
[34]
Azizi, N.; Gholibeghlo, E. Manocheri. Z. Sci. Iran., 2012, 19, 574-578.
[http://dx.doi.org/10.1016/j.scient.2011.11.043]
[35]
Kalla, R.M.N.; Hong, S.C.; Kim, I. ACS Omega, 2018, 3(2), 2242-2253.
[http://dx.doi.org/10.1021/acsomega.7b01925] [PMID: 31458526]
[36]
Wang, Y.; Yuan, Y.; Xing, C.H.; Lu, L. Tetrahedron Lett., 2014, 55, 1045-1048.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.078]
[37]
Vinay, K.P.; Pazhamalai, A. J. Org. Chem., 2017, 82, 12328-12336.
[http://dx.doi.org/10.1021/acs.joc.7b02161] [PMID: 29131624]
[38]
Ma, J.; Kass, S.R. Org. Lett., 2018, 20(9), 2689-2692.
[http://dx.doi.org/10.1021/acs.orglett.8b00900] [PMID: 29696976]
[39]
Huo, C.D.; Sun, C.G.; Wang, C.; Jia, X.D.; Chang, W.J. ACS Sustain. Chem. Eng., 2013, 1, 549-553.
[http://dx.doi.org/10.1021/sc400033t]
[40]
Yang, T.; Lu, H.; Shu, Y.; Ou, Y.; Hong, L.; Au, C.T.; Qiu, R. Org. Lett., 2020, 22(3), 827-831.
[http://dx.doi.org/10.1021/acs.orglett.9b04272] [PMID: 31913641]
[41]
Simha, P.R.; Mangali, M.S.; Gari, D.K.; Venkatapuram, P.; Adivireddy, P. J. Heterocycl. Chem., 2017, 54, 2717-2724.
[http://dx.doi.org/10.1002/jhet.2873]
[42]
Wang, L.; Wei, W.; Guo, Y.; Xu, J.; Shao, S. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2011, 78(2), 726-731.
[http://dx.doi.org/10.1016/j.saa.2010.12.004] [PMID: 21186137]
[43]
Huo, C.D.; Kang, L.S.; Xu, X.L.; Jia, X.D.; Wang, X.C.; Xie, H.S.; Yuan, Y. Tetrahedron Lett., 2014, 55, 954-958.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.055]
[44]
Ling, F.; Xiao, L.; Zhong, W.H. Org. Biomol. Chem., 2018, 16, 9274-9278.
[http://dx.doi.org/10.1039/C8OB02805B] [PMID: 30483686]
[45]
McLean, E.B.; Cutolo, F.M.; Cassidy, O.J.; Burns, D.J.; Lee, A.L. Org. Lett., 2020, 22(17), 6977-6981.
[http://dx.doi.org/10.1021/acs.orglett.0c02526] [PMID: 32845648]
[46]
Zhou, B.; Chen, Z.Z.; Zheng, Z.B.; Han, B.B.; Zou, X.Z. Synth. Commun., 2012, 42, 1445.
[http://dx.doi.org/10.1080/00397911.2010.540696]
[47]
Hojati, S.F.; Zeinali, T.; Nematdoust, Z. Bull. Korean Chem. Soc., 2013, 34, 117-120.
[http://dx.doi.org/10.5012/bkcs.2013.34.1.117]
[48]
Han, B.; Zheng, Z.; Wu, F.; Wang, A. Synth. Commun., 2017, 47, 2387-2394.
[http://dx.doi.org/10.1080/00397911.2017.1378681]
[49]
Pasha, M.A.; Jayashankara, V.P. J. Pharmacol. Toxi., 2006, 1, 585-590.
[http://dx.doi.org/10.3923/jpt.2006.585.590]
[50]
Hojati, S.F.; Zeinali, T.; Nematdoust, Z. Bull. Korean Chem. Soc., 2013, 34, 117-120.
[http://dx.doi.org/10.5012/bkcs.2013.34.1.117]

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