European Journal of Chemistry

Synthesis of bis(indolyl)methanes using molten N-butylpyridinium bromide

Article Sidebar

PDF
Published: Dec 31, 2012
DOI: https://doi.org/10.5155/eurjchem.3.4.475-479.709
Keywords:
Molten salt, Designer solvent, Aromatic aldehydes, Bis(indolyl)methanes, Condensation reaction, Electrophilic substitution reaction
Section
Research Article
Issue
Vol. 3 No. 4 (2012): December 2012
Dates
Received 2012-11-16
Accepted 2012-11-29
Published 2012-12-31


Main Article Content

Gaurav Gupta
School of Chemical Sciences, North Maharashtra University, Jalgaon, 425001, India
Ganesh Chaudhari
Department of Chemistry, Moolji Jaitha College, Jalgaon, 425001, India
Preeti Tomar
Department of Applied Chemistry, Jaywant Shikshan Prasarak Mandal’s Rajashi Shahu College of Engineering, Pune, 411027, India
Yogesh Gaikwad
Anacon Laboratories, Nagpur, 440010, India
Rameez Azad
Anacon Laboratories, Nagpur, 440010, India
Girish Pandya
Anacon Laboratories, Nagpur, 440010, India
Govinda Waghulde
Department of Chemistry, Dadasaheb Devidas Namdeo Bhole, College, Bhusawal, 425201, India
Kesharsingh Patil
School of Chemical Sciences, North Maharashtra University, Jalgaon, 425001, India

Abstract

A simple and rapid protocol has been developed for the synthesis of bis(indolyl)methane compounds in excellent yields using molten N-butyl-pyridinium bromide as a solvent and a working catalyst for the reaction. Synthesis of bis(indolyl)methane compounds were accomplished at moderate experimental conditions of temperature and ambient pressure, also involving an electrophilic substitution reaction of indoles with several aromatic aldehydes. The derivatives were confirmed with mass and other usual spectroscopic techniques. A discussion on plausible mechanism for the reaction is also presented.

3_4_475_479_800


icon graph This Abstract was viewed 2599 times | icon graph Article PDF downloaded 1173 times

How to Cite
(1)
Gupta, G.; Chaudhari, G.; Tomar, P.; Gaikwad, Y.; Azad, R.; Pandya, G.; Waghulde, G.; Patil, K. Synthesis of bis(indolyl)methanes Using Molten N-Butylpyridinium Bromide. Eur. J. Chem. 2012, 3, 475-479.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Potewar, T. M.; Kathiravan, M. K.; Chothe, A. S.; Srinivasan, K. V. Eur. J. Chem. 2011, 2(2), 235‐237.
http://dx.doi.org/10.5155/eurjchem.2.2.235-237.205

[2]. Welton, T. Chem. Rev. 1999, 99, 2071-2083.
http://dx.doi.org/10.1021/cr980032t
PMid:11849019

[3]. Fan, Y.; Zhang, S. Eur. J. Chem. 2011, 2(2), 282‐288.
http://dx.doi.org/10.5155/eurjchem.2.2.282-288.393

[4]. Angell, C.; Ansari, Y.; Zhao, Z. Faraday Discuss. 2012, 154, 9-27.
http://dx.doi.org/10.1039/c1fd00112d
PMid:22455011

[5]. Wikes, J. Green Chem. 2002, 4, 73-80.
http://dx.doi.org/10.1039/b110838g

[6]. Vivar, O.; Lin, C.; Firestone, G.; Bjeldanes, L. Biochem. Pharmacol. 2009, 78, 469-476.
http://dx.doi.org/10.1016/j.bcp.2009.05.008
PMid:19433067 PMCid:2706920

[7]. Hong, C.; Firestone, G.; Bjeldanes, L. Biochem. Pharmacol. 2002, 63, 1085-1097.
http://dx.doi.org/10.1016/S0006-2952(02)00856-0

[8]. Riby, J.; Chang, G.; Firestone, G.; Bjeldanes, L. Biochem. Pharmacol. 2000, 60, 167-177.
http://dx.doi.org/10.1016/S0006-2952(00)00307-5

[9]. Su, Y.; Vanderlaag, K.; Ireland, C.; Ortiz, J.; Grage, H.; Safe, S.; Frankel, A. Breast Cancer Res. 2007, 9(4), 1-14.
http://dx.doi.org/10.1186/bcr1761
PMid:17764562 PMCid:2206732

[10]. Sujatha, K.; Perumal, P.; Muralidharan, D.; Rajendran, M. Indian J. Chem. B 2009, 48, 267-272.

[11]. De-Kruif, C.; Marsman, J.; Venekamp, J.; Falke, H.; Noordhoek, J.; Blaauboer, B.; Wortelboer, H. Chem-Biol. Interact. 1991, 80, 303-315.
http://dx.doi.org/10.1016/0009-2797(91)90090-T

[12]. Vaghei, R.; Veisi, H.; Keyoour, H.; Firouzabadi, A. Mol. Divers. 2010, 14, 87-96.
http://dx.doi.org/10.1007/s11030-009-9150-z
PMid:19449112

[13]. Murugan, R.; Karthikeyan, M.; Perumal, P.; Reddy, B. Tetrahedron 2005, 61, 12275-12281.
http://dx.doi.org/10.1016/j.tet.2005.09.108

[14]. Heravi, M.; Bakhtiari, K.; Fatehi, A.; Bamoharram, F. Catal. Commun. 2008, 9, 289-292.
http://dx.doi.org/10.1016/j.catcom.2007.07.039

[15]. Kolvari, E.; Zolfigol, M.; Banary, H. Chin. Chem. Lett. 2011, 22, 1305-1308.
http://dx.doi.org/10.1016/j.cclet.2011.07.004

[16]. Sheikhshoaie, I.; Khabazzadeh, H.; Nia, S. Transit. Metal Chem. 2009, 34, 463-466.
http://dx.doi.org/10.1007/s11243-009-9217-9

[17]. Azizian, J.; Teimouri, F.; Mohammadizadeh, M. Catal. Commun. 2007, 8, 1117-1121.
http://dx.doi.org/10.1016/j.catcom.2006.06.002

[18]. Sharma, G.; Reddy, J.; Lakshmi, P.; Krishna, P. Tetrahedron Lett. 2004, 45, 7729-7732.
http://dx.doi.org/10.1016/j.tetlet.2004.08.084

[19]. Yang, J.; Wang, Z.; Pan, F.; Li, Y.; Bao, W. Org. Biomol. Chem. 2010, 8, 2975-2978.
http://dx.doi.org/10.1039/c004213g
PMid:20458430

[20]. Reddy, B.; Sreekanth, P.; Lakshmanan, P. J. Mol. Catal. A-Chem. 2005, 237, 93-100.

[21]. Firouzabadi, H.; Iranpoor, N.; Jafarpour, M.; Ghaderi, A. J. Mol. Catal. A-Chem. 2006, 253, 249-251.

[22]. Khabazzadeh, H.; Sheikhshoaie, I.; Nia, S. Trans. Metal Chem. 2010, 35, 125-127.
http://dx.doi.org/10.1007/s11243-009-9304-y

[23]. Ma, S.; Yu, S.; Peng, Z. Org. Biomol. Chem. 2005, 3, 1933-1936.
http://dx.doi.org/10.1039/b503378k
PMid:15889176

[24]. Wang, S.; Ji, S. Synthetic Commun. 2008, 38, 1291-1298.
http://dx.doi.org/10.1080/00397910701873318

[25]. Sarvari, M. Synthetic Commun. 2008, 38, 832-840.
http://dx.doi.org/10.1080/00397910701845274

[26]. Magesh, C.; Nagarajan, R.; Karthik, M.; Perumal, P. Appl. Catal. A-Gen. 2004, 266, 1-10.
http://dx.doi.org/10.1016/j.apcata.2004.01.024

[27]. Karthik, M.; Magesh, C.; Perumal, P.; Palanichamy, M.; Arabindoo, B.; Murugesan, V. Appl. Catal. A-Gen. 2005, 286, 137-141.
http://dx.doi.org/10.1016/j.apcata.2005.03.017

[28]. Karthik, M.; Tripathi, A.; Gupta, N.; Palanichamy, M.; Murugesan, V. Catal. Commun. 2004, 5, 371-375.
http://dx.doi.org/10.1016/j.catcom.2004.04.007

[29]. Bai, G.; Ma, Z.; Shi, L.; Li, T.; Han, J.; Chen, G.; Li, N.; Liu, P. Res. Chem. Intermed. 2012, 38(9), 2501-2510.
http://dx.doi.org/10.1007/s11164-012-0567-0

[30]. Bandagar, B.; Shaikh, K. Tetrahedron Lett. 2003, 44, 1959-1961.
http://dx.doi.org/10.1016/S0040-4039(03)00032-7

[31]. Ji, S.; Wang, S.; Zhang, Y.; Loh, T. Tetrahedron 2004, 60, 2051-2055.
http://dx.doi.org/10.1016/j.tet.2003.12.060

[32]. Naskar, S.; Paira, P.; Paira, R.; Mondal, S.; Maity, A.; Hazra, A.; Sahu, K.; Saha, P.; Banerjee, S.; Luger, P.; Webe, M.; Mondal, N. Tetrahedron 2010, 66, 5196-5203.
http://dx.doi.org/10.1016/j.tet.2010.04.084

[33]. Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075-4078.
http://dx.doi.org/10.1016/S0040-4039(02)00682-2

[34]. Chakrabarty, M.; Sarkar, S. Tetrahedron Lett. 2002, 43, 1351-1353.
http://dx.doi.org/10.1016/S0040-4039(01)02380-2

[35]. Praveen, C.; DheenKumar, P.; Muralidharan, D.; Perumal, P. Bioorg. Med. Chem. Lett. 2010, 20, 7292-7296.
http://dx.doi.org/10.1016/j.bmcl.2010.10.075
PMid:21071222

[36]. Mulla, S.; Sudalai, A.; Pathan, M.; Siddique, S.; Inamdar, S.; Chavan, S.; Reddy, S. RSC. Adv. 2012, 2, 3525-3529.

[37]. Chakraborti, A.; Raha-Roy, S.; Kumar, D.; Chopra, P. Green Chem. 2008, 10, 1111-1118.
http://dx.doi.org/10.1039/b807572g

[38]. Deb, M.; Bhuyan, P. Tetrahedron. Lett. 2006, 47, 1441-1443.
http://dx.doi.org/10.1016/j.tetlet.2005.12.093

[39]. Azizi, N.; Manocheri, Z. Res. Chem. Intermed. 2012, 38(7), 1495-1500.
http://dx.doi.org/10.1007/s11164-011-0479-4

[40]. Cham, H. C.; Koch, V. R.; Miller, L. L.; Osteryang, R. A. J. Am. Chem. Soc. 1975, 97, 3264-3265.
http://dx.doi.org/10.1021/ja00844a081

[41]. Crosthwaite, J.; Muldoon, M.; Dixon, J.; Anderson, J.; Brennecke, J. J. Chem. Thermodyn. 2005, 37, 559-568.
http://dx.doi.org/10.1016/j.jct.2005.03.013

[42]. Bandres, L.; Giner, B.; Gascon, I.; Castro, M.; Lafuente, C. J. Phys. Chem. B. 2008, 112, 12461-12467.
http://dx.doi.org/10.1021/jp805816x
PMid:18781719

[43]. Gardas, R.; Coutinho, J. Fluid Phase Equilibr. 2008, 266, 195-201.
http://dx.doi.org/10.1016/j.fluid.2008.01.021

[44]. Katritzky, A.; Lomaka, A.; Petrukhin, R.; Jain, R.; Karelson, M.; Visser, A.; Rogers, R. J. Chem. Inf. Comp. Sci. 2002, 42, 71-74.
http://dx.doi.org/10.1021/ci0100503

[45]. Letaief, S.; Detellier, C. J. Mater. Chem. 2005, 15, 4734-4740.
http://dx.doi.org/10.1039/b511282f

[46]. Wang, Z.; Zhang, L.; Cukier, R.; Bu, Y. Phys. Chem. Chem. Phys. 2010, 12, 1854-1861.
http://dx.doi.org/10.1039/b921104g
PMid:20145852

[47]. Harjani, J.; Singer, R.; Garcia, M.; Scammells, P. Green Chem. 2009, 11, 83-90.
http://dx.doi.org/10.1039/b811814k

[48]. Gupta, G.; Chaudhari, G.; Tomar, P.; Waghulde, G.; Patil K. Asian. J. Chem. 2012, 24(10), 4675-4678.

[49]. Dymon, J.; Wibby, R.; Kleingardner, J.; Tanski, J. M.; Guzei, I. A.; Holbrey, J. D.; Larsen, A. S. Dalton T. 2008, 2999-3006.

[50]. Stark, A. Top. Curr. Chem. 2009, 290, 41-81.
http://dx.doi.org/10.1007/128_2008_43
PMid:21107794

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).