[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2009.30.4.825

Alum Catalyzed Simple and Efficient Synthesis of Bis(indolyl)methanes by Ultrasound Approach

Sonar, Swapnil S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Sadaphal, Sandip A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Kategaonkar, Amol H. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Pokalwar, Rajkumar U. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Shingate, Bapurao B. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Shingare, Murlidhar S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)

Publication Information

Bulletin of the Korean Chemical Society / v.30, no.4, 2009 , pp. 825-828 More about this Journal

Abstract

Alum $(KAl(SO_4)_2{\cdot}12H_2O)$ is an inexpensive, efficient, non‐toxic and mild catalyst for the synthesis of bis(indolyl)methanes by the reaction of 1H-indole with various aldehydes/ketones under the influence of ultrasound irradiation in solvent‐free condition. The remarkable advantages of this method are the simple experimental procedures, shorter reaction times, high yields of product and green aspects by avoiding toxic catalysts and solvents.

Keywords

Bis(indolyl)methanes; Alum; 1H-indole; Aldehydes/ketones; Ultrasound irradiation;

Citations & Related Records

Times Cited By Web Of Science : 10 (Related Records In Web of Science)
Times Cited By SCOPUS : 19

Reference
Cited By SCOPUS

1	Sundberg, R. J. In The Chemistry of Indoles; Academic Press:New York, 1996; p 113.
2	Snieckus, V. In The Alkaloids; Academic Press: New York, 1968; Vol. 11, p 1.
3	Gribble, G. W. In Comprehensive Heterocyclic Chemistry, 2nd ed.; Pergamom Press: New York, 1996; Vol. 2, p 211.
4	Morris, S. A.; Anderson, R. J. Tetrahedron 1990, 46, 715. DOI ScienceOn
5	Kamal, A.; Qureshi, A. A. Tetrahedron 1963, 19, 513. DOI ScienceOn
6	Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609. DOI ScienceOn
7	Yadav, J. S.; Reddy, B. V. S.; Murthy, V. S. R.; Kumar, G. M.; Madan, C. Synthesis 2001, 783.
8	Koshima, H.; Matsuaka, W. J. Heterocyclic Chem. 2002, 39, 1089. DOI ScienceOn
9	Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 105. DOI ScienceOn
10	Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557. DOI ScienceOn
11	Ramesh, C.; Ravindranath, N.; Das, B. J. Chem. Res. Synop. 2003, 72.
12	Bandgar, B. P.; Shaikh, K. A. J. Chem. Res. Synop. 2004, 34.
13	Nagarajan, R.; Perumal, P. T. Chem. Lett. 2004, 33, 288. DOI ScienceOn
14	Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V. Catal. Commun. 2004, 5, 371. DOI ScienceOn
15	Chakrabarty, M.; Gosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075. DOI ScienceOn
16	Ji, S. J.; Zhou, M. F.; Gu, D. G.; Jiang, Z. Q.; Loh, T. P. Eur. J. Org. Chem. 2004, 1584.
17	Pnieres-Carrillo, G.; Garcia-Estrada, J. G.; Gutierrez-Ramirez, J. L.; Alvarez-Toledano, C. Green Chem. 2003, 5, 337. DOI ScienceOn
18	Yadav, J. S.; Reddy, B. V. S.; Sunitha, S. Adv. Synth. Catal. 2003, 345, 349. DOI ScienceOn
19	Ji, S. J.; Zhou, M. F.; Gu, D. G.; Wang, S. Y.; Loh, T. P. Synlett 2003, 2077.
20	Sadaphal, S. A.; Sonar, S. S.; Shingare, M. S. Central Euro. J. Chem. 2008, 6, 622. DOI ScienceOn
21	Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod. 1995, 58, 1254. DOI ScienceOn
22	Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941. DOI ScienceOn
23	Jiang, B.; Yang, C. G.; Wang, J. J. J. Org. Chem. 2002, 67, 1389.
24	Hong, C.; Firestone, G. L.; Bjeldanes, L. F. Biochem. Pharmacol. 2002, 63, 1085. DOI ScienceOn
25	Ge, X.; Yannai, S.; Rennert, G.; Gruener, N.; Fares, F. A. Biochem. Biophys. Res. Commun. 1996, 228, 153. DOI ScienceOn
26	Mason, T. J.; Lorimer, J. P. In Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry; John Wiley and Son: New York, 1988.
27	Suslick, K. S. In Ultrasound, its Chemical, Physical and Biological Effects; VCH: Weinheim, 1988.
28	Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 350. DOI ScienceOn
29	Gaplovsky, A.; Gaplovsky, M.; Toma, S.; Luche, J. L. J. Org. Chem. 2000, 65, 8444. DOI ScienceOn
30	Deshmukh, R. R.; Rajagopal, R.; Srinivasan, K. V. Chem. Commun. 2001, 544.
31	Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123. DOI ScienceOn
32	Nagawade, R. R.; Shide, D. B. Bull. Korean Chem. Soc. 2005, 26, 12.
33	Nagawade, R. R.; Shinde, D. B. Acta Chin. Slov. 2006, 53, 210.
34	Zolfigol, M. A.; Salehi, P.; Shiri, M.; Tankouchian, Z. Catal. Commun. 2007, 8, 1731.
35	Hasaninejad, A.; Zare, A.; Sharghi, H.; Niknam, K.; Shekouhya, M. Arkivoc 2007, xiv, 39.
36	Srinivasa, A.; Varma, P. P.; Hulikal, V. Monat. Fur. Chemie. 2008, 139, 111. DOI ScienceOn
37	Nezhad, A. K.; Parhami, A.; Zare, A.; Zare, A. R. M.; Hasaninejad, A.; Panahi, F. Synthesis 2008, 617.
38	Reddy, A. V.; Ravinder, R.; Reddy, V. L. N.; Goud, T. V.; Ravikanth, V.; Venkateseswarlu, Y. Synth. Commun. 2003, 33, 3687. DOI ScienceOn
39	Mohammadi, A. A.; Mivechi, M.; Kefayati, H. Monatshefte Fur Chieme 2008, 139, 935. DOI ScienceOn
40	Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Australian J. Chem. 2008, 61, 905. DOI ScienceOn
41	Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2001, 3, 310. DOI ScienceOn
42	Hangarge, R. V.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2002, 4, 266. DOI ScienceOn
43	Madje, B. R.; Patil, P. T.; Shindalkar, S. S.; Benjamin, S. B.; Dongare, M. K.; Shingare, M. S. Catalysis Commun. 2004, 5, 353. DOI ScienceOn
44	Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467. DOI ScienceOn
45	Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229. DOI ScienceOn
46	Mi, X. L.; Luo, S. Z.; He, J. Q.; Cheng, J. P. Tetrahedron Lett. 2004, 45, 4567. DOI ScienceOn
47	Feng, X. L.; Guan, C. J.; Zhao, C. X. Synth. Commun. 2004, 34, 487. DOI ScienceOn
48	Wang, L. M.; Han, J. W.; Tian, H.; Sheng, J.; Fan, Z. Y.; Tang, X. P. Synlett 2005, 337.
49	Tanaka, K. F. Chem. Rev. 2000, 100, 1025. DOI ScienceOn
50	Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. Applied Catalysis 2006, 300, 85. DOI ScienceOn
51	Dabiri, M.; Baghbanzadeh, M.; Kiani, S.; Vakilzadeh, Y. Monatshefte Fur Chieme 2007, 138, 997. DOI ScienceOn
52	Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. Monatshefte Fur Chieme, 2007, 138, 1253. DOI ScienceOn
53	Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M. S.; Arzroomchilar, E. Bioorg. Med. Chem. Lett. 008, 18, 436. DOI ScienceOn
54	Mahajan, D.; Nagvi, T.; Sharma, R. L.; Kapoor, K. K. Australian J. Chem. 2008, 61, 159. DOI ScienceOn
55	Pawar, S. S.; Uppalla, L. S.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 5858. DOI ScienceOn
56	Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 4252. DOI ScienceOn

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8	Samuel R. Mendes. (2015) Green Chemistry Synthesis of bis(indolyl)methanes using ammonium niobium oxalate (ANO) as an efficient and recyclable catalyst / 17 (8) , 4334
3	Hoda Banari. (2017) Research on Chemical Intermediates Efficient synthesis of bis(indolyl)methanes, bispyrazoles and biscoumarins using 4-sulfophthalic acid / 43 (3) , 1635
1	(2018) Monatshefte für Chemie - Chemical Monthly Synthesis of symmetric triarylmethane derivatives catalyzed by AIL ionic liquid / 149 (1) , 57
5	(2018) Synthetic Communications -heterocycles / 48 (5) , 473
36	Swapnil S. Sonar. (2009) ChemInform ChemInform Abstract: Alum Catalyzed Simple and Efficient Synthesis of Bis(indolyl)methanes by Ultrasound Approach. / 40 (36)
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4	GANESAN SHUNMUGADHAS SURESH KUMAR. (2009) Journal of chemical sciences Potash alum [KAl(SO 4 ) 2 .12H 2 O] catalysed esterification of formylphenoxyaliphatic acids / 124 (4) , 857
5	(2010) Ultrasonics sonochemistry Solvent-free sonochemical preparation of +/--aminophosphonates catalyzed by 1-hexanesulphonic acid sodium salt / 17 (5) , 760
6	(2009) Bulletin of the Korean Chemical Society An Efficient Synthesis of 3,4-Dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine Derivatives Catalyzed by Zirconyl(IV) Chloride and Evaluation of its Biological Activities / 31 (6) , 1657
14	V. Jhansi Rani. (2009) Synthetic communications PEG-SO3H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media / 42 (14) , 2048
3	Asok K. Mallik. (2009) Green chemistry letters and reviews A convenient, eco-friendly, and efficient method for synthesis of bis(3-indolyl)methanes “on-water” / 5 (3) , 321
13	Vijay Vilas Shinde. (2009) Synthetic communications Ultrasound-assisted synthesis of diversely functionalized tetrahydro-1H-Indole-4(5H)-one using Brønsted base silica sodium carbonate (SSC) as a catalyst under solvent-free conditions / 46 (13) , 1145
90	(2009) RSC advances Metal free synthesis of tetrahydrobenzo[a]xanthenes using orange peel as a natural and low cost efficient heterogeneous catalyst / 6 (90) , 87082
None	Chandrabhan Verma. (2009) Journal of the association of arab Universities for basic and applied sciences A thermodynamical, electrochemical and surface investigation of Bis (indolyl) methanes as Green corrosion inhibitors for mild steel in 1M hydrochloric acid solution / 21 (None) , 24
2	(2009) ACS omega Synthesis of Bis(indolyl)methanes Using Hyper-Cross-Linked Polyaromatic Spheres Decorated with Bromomethyl Groups as Efficient and Recyclable Catalysts / 3 (2) , 2242
None	(2009) Current organic chemistry Recent Developments on the Synthesis of Biologically Significant bis/tris(indolyl)methanes under Various Reaction Conditions: A Review / 24 (None) , 583

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