Journal Articles (All Issues)

ALUM CATALYZED GREEN SYNTHESIS OF BIS-INDOLYLMETHANES IN POLYETHYLENE GLYCOL AND WATER USING MICROWAVE IRRADIATION

Authors

Dhruva Kumar,1 Rajesh Kumar2 & Jagir S Sandhu3

Keyword Alum, indole, carbonyl compounds, bis(indolyl)methanes, water, Microwave irradiation

Abstract

A sustainable approach to synthesize bis-indolylmethanes by employing alum as a catalyst, with polyethylene glycol (PEG) and water serving as environmentally friendly solvents. Microwave irradiation (MWI) significantly accelerates the reaction, leading to improved yields and shorter reaction times. The method not only reduces environmental impact but also proves cost-effective, demonstrating its potential for practical applications in sustainable synthesis.

References

    1 (b) Sundberg R J, The Chemistry of Indoles; Academic Press, New York, 1996, p 113. (b) Shirini, F.; Fallah-Shojaei, A.; Samavi, L.; Abedini, M. RSC Adv. 2016, 6, 48469-48478. https://doi.org/10.1039/C6RA04893E. 2 (a) Siadatifard, S. H.; Abdoli-Senejani, M.; Bodaghifard, M. A.; Weaver, G. Cogent Chemistry 2016, 2(1), https://doi.org/10.1080/23312009.2016.1188435. (b) Osawa T & Namiki M, Tetrahedron Lett, 24, 1983, 4719; (c) Fahy E, Potts B C M, Faulkner D J & Smith K, J Nat Prod, 54, 1991, 564; (d) Bell R, Carmeli S & Sar N, J Nat Prod, 57, 1994, 1587; (e) Garbe T R, Kobayashi M, Shimizu N, Takesue N, Ozawa M & Yukawa H, J Nat Prod, 63, 2000, 596. (f) Mathavan, S.; Kannan, K.; Yamajala, R. B. R. D.; Org. Biomol. Chem. 2019, 17 (44), 9620-9626. https://doi.org/10.1039/c9ob02090j. (g) Yuan, X.; Wu, L.; Xu, C.; Pan, Z.; Shi, L.; Yang, G.; Wang, C.; Fan, S. Tetrahedron Lett.2019, 60 (52), 151329. https://doi.org/10.1016/j.tetlet.2019.151329. 3 Hong C, Firestone G L & Bjeldanes L F, Biochem Pharmacol, 63, 2002, 1085. 4 (a) Gregorovich B V, Liang K, Clugston M & Macdonald S, Can J Chem, 46, 1968, 3291; (b) Roomi M & Macdonald S, Can J Chem 48, 1970, 139; (c) Auria M, Tetrahedron, 47, 1991, 9225. 5 (a) Chatterjee A, Manna S, Benerji J, Pascard C, Prange T & Shoolery J, J Chem Soc Perkin Trans 1, 1980, 553; (b) Noland W E, Venkiteswaran M R & Richards C G, J Org Chem, 26, 1961, 4241; (c) Wang Y M, Wen Z, Chen X M, Du D M, Matsuura T & Meng J B, J Heterocycl Chem, 35, 1998, 313. 6 (a) He X, Hu S, Liu K, Guo Y, Xu J & Shao S, Org Lett, 8, 2006, 333; (b) Nagarajan R & Perumal P T, Chem Lett, 33, 2004, 288; (c) Bartoli G, Bosco M, Foglia G, Giuliani A, Marcantoni E & Sambri L, Synthesis, 2004, 895; (d) Yadav J S, Subba Reddy B V, Murthy Ch V S R, Kumar G M & Madan Ch, Synthesis, 2001, 783; (e) Mo L-P, Ma Z-C & Zhang Z-H, Synth Commun, 35, 2005, 1997. 7 (a) Zhang Z-H, Yin L & Wang Y-M, Synthesis, 2005, 1949; (b) Yadav J S, Reddy B V S & Sunitha S, Adv Synth Catal, 345, 2003, 349; (c) Ji S-J, Zhou M-F, Gu D-G, Jiang Z-Q & Loh T-P, Eur J Org Chem, 2004, 1584; (d) Bavanthula R, Reddy P N, Kumar B S, Neeladri S, Reddy Y & Reddy T, J Chem Res (S), 2005, 222. 8 (a) Ramesh C, Ravindranath N & Das B, J Chem Res (S), 2003, 72; (b) Nagarajan R & Perumal P T, Synth Commun, 32, 2002, 105; (c) Li W-J, Lin X-F, Wang J, Li G-L & Wang Y-G, Synth Commun, 35, 2005, 2765; (d) Babu G, Sridhar N & Perumal P T, Synth Commun, 30, 2000, 1609. 9 (a) Nagarajan R & Perumal P T, Tetrahedron, 58, 2002, 1229; (b) Feng X L, Guan C J & Zhao C X, Synth Commun, 34, 2004, 487; (c) Chakrabarty M, Gosh N, Basak R & Harigaya Y, Tetrahedron Lett, 37, 1996, 4467; (d) Ke B, Qin Y, Wang Y & Wang F, Synth Commun, 35, 2005, 1209. 10 (a) Ramesh C, Banerjee J, Pal R & Das B, Adv Synth Catal, 345, 2003, 557; (b) Bandgar B P & Shaikh K A, Tetrahedron Lett, 44, 2003, 1959; (c) Koshima H & Matsusaka W, J Heterocycl Chem, 39, 2002, 1089. 11 Gu D G, Ji S J, Jiang Z Q, Zhou M F & Loh T P, Synlett, 2005, 959. 12 (a) Mi X L, Luo S Z, He J Q & Chen J P, Tetrahedron Lett, 45, 2004, 4567; (b) Wang L, Han J, Tian H, Sheng J, Fan Z & Tang X, Synlett, 2005, 337; (c) Deb M L & Bhuyan P J, Tetrahedron Lett, 47, 2006, 1441. 13 Azizian J, Mohammadi A A, Karimi A R & Mohammadizadeh M R, Applied Catal A: General, 300, 2006, 85. 14 Dabiri M, Baghbanzadeh M, Kiani S & Vakilzadeh Y, Monatsh Chem, 138, 2007, 997. 15 Azizian J, Mohammadi A A, Karimi A R & Mohammadizadeh M R, J Org Chem, 71, 2006, 350. 16 Dabiri M, Salehi P, Otokesh S Baghbanzadeh M, Kozehgary G & Mohammadi A A, Tetrahedron Lett, 46, 2005, 6123. 17 Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M & Bahramnejad M, Monatsh Chem, 138, 2007, 1253. 18 Azizian J, Mohammadi A A, Karimi A R & Mohammadizadeh M R, J Chem Res (S), 6, 2004, 424. 19 Azizian J, Mohammadi A A, Karimi A R, Mohammadizadeh M R & Koohshari M, Heterocycles, 63, 2004, 2013. 20 Mahajan D, Naqvi T, Sharma R L & Kapoor K K, Australian J Chem, 61, 2008, 159. 21 Bhuyan P J, Borah R C & Sandhu J S, Tetrahedron Lett, 30, 1989, 1421. 22 Gohain S, Prajapati D & Sandhu J S, Chem Lett, 1995, 725. 23 Deb M L & Bhuyan P J, Synlett, 2008, 325.

Downloads

View/Download PDF

PDF



Published

2021-01-30

Issue

Vol. 40 No. 01 (2021)