Abstract
Trichloroisocyanouric acid (TCCA)-functionalized mesoporous silica nanocomposites (SBA/ TCCA) were synthesized and characterized for the acylation of indole. The uniform incorporation of TCCA inside the SBA-15 matrix was confirmed by standard characterization techniques (PXRD, Adsorption studies, FT-IR, etc.). The catalytic activity studies of SBA/TCCA nanocomposites for acylation of indole showed high selectivity (60–90%) of the 3-acetyl indole compared to homogeneous TCCA (50%). The advantage of solid support for higher selectivity is also explained.
Similar content being viewed by others
References
Wight A P and Davis M E 2002 Chem. Rev. 102 3589
Hoelderich W F 2000 Catal. Today 62 115
Sheldon R A 1997 Chem. Ind. 12 12
Corma A 1997 Chem. Rev. 97 2373
Sachdev D and Dubey A 2013 Catal. Commun. 39 39
Sachdev D, Wilson G R, Srivastava N M and Dubey A 2014 Catal. Commun. 51 90
Sachdev D, Dubey A, Wilson G R and Sharma A 2015 New J. Chem. 39 2633
Fujioka H, Murai K, Kubo O, Ohba Y and Kita Y 2007 Tetrahedron 63 638
Ye Y, Wang Y, Liu R, Zhang G, Zhang Q, Chen J and Liang X 2003 Chem. Commun. 21 2714
Zolfigol M A, Ghaemi E and Madrakian E 2003 Synlett 44 191
Akhlaghinia B, Pourali A R and Rahman M 2012 Synth. Commun. 42 1184
Albert D H, Luo G, Magoc T J, Tapang P, Holms J H, Davidsen S K, Summers J B and Carter G W 1996 Shock 6 112
Keasling H, Willette R and Szmuszkovicz J 1964 J. Med. Chem. 7 94
Garratt P J, Vonhoff S, Rowe S J and Sugden D 1994 Med. Chem. Lett. 4 1559
Kumar D, Kumar N M, Chang K H and Shah K 2010 Eur. J. Med. Chem. 45 4664
Kumar D, Kumar N M, Akamatsu K, Kusaka E, Harada H and Ito T 2010 Bioorg. Med. Chem. 20 3916
Bergman J and Venemalm L 1990 Tetrahedron 46 6061
Yang C X, Patel H H, Ku Y Y, Shah R and Sawick D 1997 Synth. Commun. 27 2125
Ketcha D M and Gribbe G W 1985 J. Org. Chem. 50 5451
Eyley S C, Giles R G and Heany H 1985 Tetrahedron Lett. 26 4649
Ottoni O, Neder A V F, Dias A K B, Cruz R P A and Aquino L B 2001 Org. Lett. 3 1005
Bai G, Li T, Yang Y, Zhang H, Lan X, Li F, Han J, Ma Z, Chen Q and Chen G 2012 Catal. Commun. 29 114
Kamal A and Qureshi A A 1963 Tetrahedron 19 513
Kruk M, Jaroniec M, Ko C H and Ryoo R 2000 Chem. Mater. 12 1961
Yokoi T, Yoshitake H and Tatsumi T 2004 J. Mater. Chem. 14 951
Rosenholm J M and Lindén M 2007 Chem. Mater. 19 5023
Acknowledgment
AD thanks MANIT-Bhopal for help and support.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information (SI)
Supplementary information includes the PXRD pattern of SBA/3TCCA (Figure S1), pore size distribution curve of (a) SBA-15 and (b) SBA/1.5TCCA & (c) SBA/ 2TCCA nanocomposites (Figure S2), N2 adsorption-desorption isotherms (Figure S3) of SBA/3TCCA nanocomposites, SEM images (Figure S4) of (a) SBA-15 & (b) SBA/1.5TCCA nanocomposites and reusability data (Figure S5) of SBA/1.5TCCA catalyst. Supplementary information is available at www.ias.ac.in/chemsci.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
WILSON, G.R., DUBEY, A. Synthesis and characterization of Trichloroisocyanouric acid functionalized mesoporous silica nanocomposite (SBA/TCCA) for the Acylation of Indole. J Chem Sci 128, 1285–1290 (2016). https://doi.org/10.1007/s12039-016-1131-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-016-1131-z