Efficient synthesis of bis(indolyl)methanes by the alkylation of indoles with alcohols using heterogeneous CuFe2O4 catalyst
Abstract
Keywords
Full Text:
PDFReferences
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.
DOI: https://doi.org/10.51316/jca.2021.057
Refbacks
- There are currently no refbacks.
*******
Index: Google Scholar; Crossref
---------
Vietnam Journal of Catalysis and Adsorption
Address: Room 302 | C4-5 | Hanoi University of Science and Technology. 1 Dai Co Viet, Hanoi.
Tel.: +84. 967.117.098 (Dr. Phượng) | Email: editor@jca.edu.vn | FB: JCA.VNACA