European Journal of Chemistry

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



Main Article Content

Gaurav Gupta
Ganesh Chaudhari
Preeti Tomar
Yogesh Gaikwad
Rameez Azad
Girish Pandya
Govinda Waghulde
Kesharsingh Patil

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.

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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.

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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

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