Efficient synthesis of bis(indolyl)methanes by the alkylation of indoles with alcohols using heterogeneous CuFe2O4 catalyst

Ha Minh Tuan; Bui Hoang Yen; Nguyen Ngoc Khanh; Ngo Thi Thuan; Tran Quang Hung; Vu Xuan Hoan; Dang Thanh Tuan

doi:10.51316/jca.2021.057

Authors

Ha Minh Tuan Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam
Bui Hoang Yen Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam
Nguyen Ngoc Khanh Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam
Ngo Thi Thuan Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam
Tran Quang Hung Institute of Chemistry, Vietnam Academy of Science and Technology
Vu Xuan Hoan Vietnam Petroleum Institute
Dang Thanh Tuan Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam

DOI:

https://doi.org/10.51316/jca.2021.057

Keywords:

CuFe2O4 catalyst, Sustainable process, Alkylation, Bifunctional catalysis, Indole functionalization Bis(3-indolyl)methane synthesis

Abstract

Bis(3-indolyl)methanes (BIM) are highly valuable and appear in the core structure of many natural products and pharmacologically active compounds (anticancer, anti-inflammatory, antiobesity, antimetastatic, antimicrobial, etc.). Herein, we have disclosed an air stable and highly efficient CuFe₂O₄ heterogeneous catalyst for alkylation of indoles with alcohols to give bis(3-indolyl)methanes in very good yields. The CuFe₂O₄ catalyst has been found to be magnetically recycled at least five times without losing significant catalytic activity.

Downloads

Download data is not yet available.

References

R. J. Sundberg, Indoles, Academic Press, San Diego, 1996.

J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172. https://doi.org/10.1021/ja017255c;

Y. C. Wan, Y. H. Li, C. X. Yan, M. Yan, Z. L. Tang, Eur. J. Med. Chem. 2019, 183, 111691. https://doi.org/https://doi.org/10.1016/j.ejmech.2019.111691.

Y. Zhang, X. R. Yang, H. Zhou, S. L. Li, Y. Zhu, Y. Li, Org. Chem. Front. 2018, 5, 2120. https://doi.org/10.1039/C8QO00341F;

F. Ling, L. Xiao, L. Fang, C. Feng, Z. Xie, Y. Lv, W. Zhong, Org. Biomol. Chem. 2018, 16, 9274. https://doi.org/10.1039/C8OB02805B;

R. R. Jella, R. Nagarajan, Tetrahedron 2013, 69, 10249. https://doi.org/https://doi.org/10.1016/j.tet.2013.10.037.

M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Chem. Rev. 2010, 110, 2250. https://doi.org/10.1021/cr900195a.;

S. Wang, K. Fang, G. Dong, S. Chen, N. Liu, Z. Miao, J. Yao, J. Li, W. Zhang, C. Sheng, J. Med. Chem. 2015, 58, 6678. https://doi.org/https://doi.org/10.1016/j.ejmech.2014.10.065;

M.-Z. Zhang, Q. Chen, G.-F. Yang, Eur. J. Med. Chem. 2015, 89, 421https://doi.org/https://doi.org/10.1016/j.ejmech.2014.10.065;

S. B. Bharate, J. B. Bharate, S. I. Khan, B. L. Tekwani, M. R. Jacob, R. Mudududdla, R. R. Yadav, B. Singh, P. R. Sharma, S. Maity, B. Singh, I. A. Khan, R. A. Vishwakarma, Eur. J. Med. Chem. 2013, 63, 435. https://doi.org/https://doi.org/10.1016/j.ejmech.2013.02.024;

M. Marrelli, X. Cachet, F. Conforti, R. Sirianni, A. Chimento, V. Pezzi, S. Michel, G. A. Statti, F. Menichini, Nat. Prod. Res. 2013, 27, 2039. https://doi.org/10.1080/14786419.2013.824440.;

J. Lee, Nutr. Cancer 2019, 71, 992. https://doi.org/10.1080/01635581.2019.1577979.

J. A. Joule, K. Mills, Heterocyclic Chemistry, 5th ed., Wiley, UK, 2020. https://doi.org/10.1201/9781003072850;

G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875. https://doi.org/10.1021/cr0505270.;

S. L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190. https://doi.org/10.1039/B817310A.

M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed. 2009, 48, 9608. https://doi.org/10.1002/anie.200901843.;

M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Chem. Rev. 2010, 110, 2250. https://doi.org/10.1021/cr900195a.

X. Liu, S. Ma, P. H. Toy, Org. Lett. 2019, 21, 9212. https://doi.org/10.1021/acs.orglett.9b03578;

T. Yang, H. Lu, Y. Shu, Y. Ou, L. Hong, C.-K. Au, R. Qiu, Org. Lett. 2020, 22, 827. https://doi.org/10.1021/acs.orglett.9b03578;

C. D. Huo, C. G. Sun, C. Wang, X. D. Jia, W. J. Chang, ACS Sustainable Chem. Eng. 2013, 1, 549. https://doi.org/10.1021/sc400033t;

S. Bayindir, N. A, Saracoglu, RSC Adv. 2016, 6, 72959. https://doi.org/10.1039/C6RA16192H;

G. M. Shelke, V. K. Rao, R. K. Tiwari, B. S. Chhikara, K. Parang, A. Kumar, RSC Adv. 2013, 3, 22346. https://doi.org/10.1039/C3RA44693J;

T. A. Grigolo, S. Denofre, F. Manarin, G. V. Botteselle, P. Brandão, A. Amaral, E. A. de Campos, Dalton Trans. 2017, 46, 15698. https://doi.org/10.1039/C7DT03364H.

S. Whitney, R. Grigg, A. Derrick, A. Keep, Org. Lett. 2007, 9, 3299. https://doi.org/10.1021/ol071274v.

S. Zhang, W. Fan, H. Qu, C. Xiao, N. Wang, L. Shu, Q. Hu, L. Liu, Curr. Org. Chem. 2012, 16, 942. https://doi.org/10.2174/138527212800194827;

A. E. Putra, K. Takigawa, H. Tanaka, Y. Ito, Y. Oe, T. Ohta, Eur. J. Org. Chem. 2013, 6344. https://doi.org/10.1002/ejoc.201300744;

N. Biswas, R. Sharma and D. Srimani, Adv. Synth. Catal., 2020, 362, 2902. https://doi.org/10.1002/adsc.202000326.

H. Hikawa, Y. Yokoyama, RSC Adv. 2013, 3, 1061. https://doi.org/10.1039/C2RA21887A.

S. Badigenchala, D. Ganapathy, A. Das, R. Singh, G. Sekar, Synthesis 2014, 46, 101. https://doi.org/10.1055/s-0033-1340052.

V. Polshettiwar, R. S. Varma, Green Chem. 2010, 12, 743. https://doi.org/10.1039/B921171C;

C. Descorme, P. Gallezot, C. Geantet, C. George, ChemCatChem 2012, 4, 1897. https://doi.org/10.1002/cctc.201200483.;

P. Munnik, P. E. de Jongh, K. P. de Jong, Chem. Rev. 2015, 115, 6687. https://doi.org/10.1021/cr500486u;

L. Liu, A. Corma, Chem. Rev. 2018, 118, 4981. https://doi.org/10.1021/acs.chemrev.7b00776.

R. R. Hosseinzadeh‐Khanmiri, Y. Kamel, Z. Keshvari, A. Mobaraki, G. H. Shahverdizadeh, E. Vessally, M. Babazadeh, Appl. Organomet. Chem. 2018, 32, e4452. https://doi.org/10.1002/aoc.4452.

H. Mohammadi, H. R. Shaterian, ChemistrySelect 2019, 4, 8700. https://doi.org/10.1002/slct.201901586.

R. Hudson, Y. Feng, R. S. Varma, A, Moores, Green Chem. 2014,16, 4493. https://doi.org/10.1039/C4GC00418C;

N. Yan, C. Xiao, Y. Kou, Coord. Chem. Rev. 2010, 254, 1179. https://doi.org/10.1016/j.ccr.2010.02.015.

N. Panda, A. K. Jena, S. Mohapatra, Chem. Lett. 2011, 40, 956. https://doi.org/10.1246/cl.2011.956;

N. Panda, A. K. Jena, S. Mohapatra, S. R. Rout, Tetrahedron Lett. 2011, 51, 1924. https://doi.org/https://doi.org/10.1016/j.tetlet.2011.02.050;

R. Zhang, J. Liu, S. Wang, J. Niu, C. Xia, W. Sun, ChemCatChem 2011, 3, 146. https://doi.org/10.1002/cctc.201000254;

K. Swapna, S. N. Murthy, M. T. Jyothi, Y. V. D. Nageswar, Org. Biomol. Chem. 2011, 5989. https://doi.org/10.1039/C1OB05597F.;

R. Hudson, Synlett 2013, 24, 1309. https://doi.org/10.1055/s-0033-1338949.

P. N. Amaniampong, Q. T. Trinh, J. J. Varghese, R. Behling, S. Valange, S. H. Mushrif, F. Jérôme, Green Chemistry 2018, 20, 2730. https://doi.org/10.1039/C8GC00961A.

P. N. Amaniampong, Q. T. Trinh, K. De Oliveira Vigier, D. Q. Dao, N. H. Tran, Y. Wang, M. P. Sherburne, F. Jérôme, J. Am. Chem. Soc., 2019, 141, 14772. https://doi.org/10.1039/C8GC00961A.

Q. T. Trinh, B. K. Chethana, S. H. Mushrif, J. Phys. Chem. C 2015, 119, 17137. https://doi.org/10.1021/acs.jpcc.5b03534.

J. E. De Vrieze, J. W. Thybaut, M. Saeys, ACS Catal. 2018, 8, 7539. https://doi.org/10.1021/acscatal.8b01652.

C. Sarkar, S. Pendem, A. Shrotri, D. Q. Dao, P. P. T. Mai, T. N. Nguyen, D. R. Chandaka, T. V. Rao, Q. T. Trinh, M. P. Sherburne, J. Mondal, ACS Appl. Mater. Interfaces 2019, 11, 11722. https://doi.org/10.1021/acsami.8b18675.

R. Singuru, Q. T. Trinh, B. Banerjee, B. G. Rao, L. Bai, A. Bhaumik, B. M. Reddy, H. Hirao, J. Mondal, ACS Omega 2016, 1, 1121. https://doi.org/10.1021/acsomega.6b00331.

M. Schlangen, H. Schwarz, Hel. Chim. Acta 2008, 91, 379. https://doi.org/10.1002/hlca.200890043.

Q. T. Trinh, J. Yang, J. Y. Lee, M. Saeys, J. Catal. 2012, 291, 26. https://doi.org/10.1016/j.jcat.2012.04.001.

P. N. Amaniampong, Q. T. Trinh, B. Wang, A. Borgna, Y. Yang, S. H. Mushrif, Angew. Chem. Int. Ed. 2015, 54, 8928. https://doi.org/10.1002/ange.201503916.