Abstract
An eco-friendly and expedient procedure for one-pot synthesis of bis-(indolyl)methane derivatives via electrophilic substitution reaction at C-3 position of indole with various aldehydes has been developed by using silica-diphenic acid as a novel heterogeneous catalyst. This method has various promising features such as short reaction time, easy work-up procedure, good yield of products and remarkable activity and selectivity of the catalyst.
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Kaishap P and Dohutia C 2013 Int. J. Pharm. Sci. Res. 4 1312
Lounasmaa M and Tolvanen A 2000 Nat. Prod. Rep. 17 175
Garbe T R, Kobayashi M, Shimizu N, Takesue N, Ozawa M and Yukawa H 2000 J. Nat. Prod. 63 596
Hong C, Firestone G L and Bjeldance L F 2002 Bio. Chem. Pharmacol. 63 1085
Hibino S and Choshi T 2001 Nat. Prod. Rep. 18 66
Povszsz L, Katakin G P, Foleat S and Malkovics B 1996 Acta. Phys. Acad. Sci. 29 299
Karthik M, Tripathi A K, Gupta N M, Palanichamy M and Murugeson V 2004 Catal. Commun. 5 371
Marrelli M, Cachet X, Conforti F, Sirianni R, Chimento A, Pezzi V, Michel S, Statti G A and Menichini F 2013 Nat. Prod. Res. 27 2039
Tayebee R, Amini M N, Nehzat F, Sadeghi O and Armaghan M 2013 J. Mol. Catal. A: Chem. 366 140
Shirini F and Khaligh N G 2013 Chin. J. Catal. 34 1890
Kumar V, Singh C, Sharma U, Verma P K, Singh B and Kumar N 2014 Ind. J. Chem. 53B 83
Zarea A R M, Borazjanib M P and Nazb Z 2014 Iran. Chem. Commun. 2 34
Mendes S R, Thurow S, Fortes M P, Penteado F, Lenardao E J, Alves D, Perin G and Jacob R G 2012 Tetrahedron Lett 53 5402
Pawar B, Shinde V and Chaskar A 2013 Green Sustainable Chem 3 56
Alinezhad H and Haghighi A H 2012 Caspian J. Chem. 1 1
Prasanna T S R and Raju K M 2012 J. Korean. Chem. Soc. 56 74
Giri B Y, Devi B L A P, Vijayalakshmi K, Prasad R B N, Lingaiah N and Prasad P S S 2012 Ind. J. Chem. 51B 1731
Tayebee R and Razib M K 2014 Res. Rev: J. Mater. Sci. 2 13
Hojati S F, Zeinali T and Nematdoust Z 2013 Bull. Korean Chem. Soc. 34 117
Xu X F and Xiong Y 2014 Chin. Chem. Lett. 25 406
Gupta G, Chaudhari G, Tomar P, Gaikwad Y, Azad R, Pandya G, Waghulde G and Patil K 2012 Eur. J. Chem. 3 475
Hasaninejad A, Shekouhy M, Zare A, Ghattali S M S H and Golzara N 2011 J. Iran. Chem. Soc. 8 411
Nagarajan R and Perumal P T 2002 Synth. Commun. 32 105
Bandgar B P, Bettigeri S A and Joshi N S 2004 Monatsh. Chem. 135 1265
Pore D M, Desai U V, Thopate T S and Wadgaonkar P P 2006 ARKIVOC xii 75
Pal R, Khannobis S and Sarkar T 2013 Chem. J. 3 7
Olyaei A, Vaziri M, Razeghi R, Shams B and Bagheri H 2013 J. Serb. Chem. Soc. 78 463
Prats A E P, Bernini M C, Medina M E, Torres E L, Puebla E., Monge M A and Snejko N 2011 Cryst. Eng. Comm. 13 4965
Dietzel P D C, Bloma R and Fjellvag H 2006 Dalton Trans 586
Kour G, Gupta M, Paul S, Rajnikant and Gupta V K 2014 J. Mol. Catal. A: Chem. 392 260
Li J T and Sun S F 2010 Eur. J. Chem. 7 922
Kaishap P P, Dohuti C and Chetia D 2012 Int. J. Pharm. Sci. Res 3 4247
Qu H E, Xiao C, Wang N, Yu K H, Hu Q S and Liu L X 2011 Molecules 16 3855
Behbahani F K and Sasani M 2012 J. Serb. Chem. Soc. 77 1157
Acknowledgements
We are grateful to Director, IIIM, Jammu, for recording mass spectral data and also extend my sincere thanks to Department of Chemistry, University of Jammu, for recording 1H-NMR, 13C-NMR, and IR spectral data of products and TGA and IR of the catalyst. We are also thankful to IIT Bombay for SEM and TEM studies of the catalyst.
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The 1H-NMR, 13C-NMR, and mass spectra of 2-Flourophenyl-3, 3 '-bis-(indolyl) methane have been shown in the supplementary information available at www.ias.ac.in/chemsci.
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VAID, R., GUPTA, M., CHAMBYAL, O.S. et al. SiO2-Diphenic acid: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of bis-(indolyl)methane derivatives in liquid phase. J Chem Sci 127, 987–997 (2015). https://doi.org/10.1007/s12039-015-0859-1
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DOI: https://doi.org/10.1007/s12039-015-0859-1