European Journal of Chemistry

Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water

Article Sidebar

PDF
Published: Dec 31, 2015
DOI: https://doi.org/10.5155/eurjchem.6.4.410-416.1312
Keywords:
Alum, Water, Aldehyde, Rhodanine, Triethyl amine, Microwave-assisted synthesis
Section
Research Article
Issue
Vol. 6 No. 4 (2015): December 2015
Dates
Received 2015-08-22
Accepted 2015-09-19
Published 2015-12-31


Main Article Content

Santosh Jadhav
Department of Chemistry, Vivekanand College, Aurangabad, MS, 431001, India
Mahesh Shioorkar
Department of Chemistry, Vivekanand College, Aurangabad, MS, 431001, India
Omprakash Chavan
Department of Chemistry, Barwale College, Jalna, MS, 431203, India
Aniket Sarkate
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431001, India
Devanand Shinde
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431001, India
Rajendra Pardeshi
Department of Chemistry, Sant Ramdas College, Ghansawangi, Jalna, MS, 431203, India

Abstract

An efficient and environmentally benign method has been developed for the synthesis of 5-arylidine-2-(methylthio)-thiazolones derivatives using Alum [KAl(SO4)2·12H2O] catalyst and triethyl amine in water under microwave irradiation. This green transformation generated one C-S and one C-C bond, condensation and S-methylation. Notable advantages for the present protocol include, short reaction time, cleaner reaction profile and easy isolation of product by microwave irradiation technique using green catalyst and solvent.


icon graph This Abstract was viewed 2269 times | icon graph Article PDF downloaded 1065 times

How to Cite
(1)
Jadhav, S.; Shioorkar, M.; Chavan, O.; Sarkate, A.; Shinde, D.; Pardeshi, R. Alum [KAl(SO4)2•12H2O] Catalyzed Microwave Assisted Synthesis of 5-Arylidine-2-(methylthio)-Thiazolone Derivatives in Water. Eur. J. Chem. 2015, 6, 410-416.

Article Details

Share
Links for Article


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

[1]. Breslow, R.; Anastas, P. T.; Williamson, T. C. Oxford Press, New York, 1998.

[2]. Sheldon, R. A. Green Chem. 2005, 7, 267-278.
http://dx.doi.org/10.1039/b418069k

[3]. Walsh, P. J.; Li, H.; Anaya, P. C. Chem. Rev. 2007, 107, 2503-2545.
http://dx.doi.org/10.1021/cr0509556

[4]. Caddic, K. S. Tetrahedron 1995, 51, 38, 10403-10432.
http://dx.doi.org/10.1016/0040-4020(95)00662-R

[5]. Sethuraman, I.; Subbu, P.; Natarajan, A. Green Chem. 2012, 14, 3361-3367.
http://dx.doi.org/10.1039/c2gc36040c

[6]. Pramod, K. Curr. Microwave Chem. 2015, 2, 144-149.
http://dx.doi.org/10.2174/2213335601666141126220412

[7]. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. Appl. Catal. 2006,300, 85-88
http://dx.doi.org/10.1016/j.apcata.2005.11.001

[8]. Dabiri, M.; Baghbanzadeh, M.; Kiani, S.; Vakilzadeh, Y. Monatsh. Chem. 2007, 138, 997-999.
http://dx.doi.org/10.1007/s00706-007-0666-6

[9]. Madje, B. R.; Ubale, M. B.; Bharad, J. V.; Shingare, M. S. S. Afr. J. Chem. 2010, 63, 158-161.

[10]. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Org. Chem. 2006, 71, 350-352.

[11]. Mohammadi, A. A.; Mivechi, M.; Kefayati, H. Monatsh. Chem. 2008, 139, 935-937.
http://dx.doi.org/10.1007/s00706-008-0875-7

[12]. Mohammadi, A. A.; Qaraat, H.; Monatsh. Chem. 2009, 140, 401-404.
http://dx.doi.org/10.1007/s00706-008-0040-3

[13]. Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Bahramnejad, M. Monatsh. Chem. 2007,138, 1253-1255.
http://dx.doi.org/10.1007/s00706-007-0724-0

[14]. Mahajan, D.; Naqvi, T.; Sharma, R. L.; Kapoor, K. K. Aust. J. Chem. 2008, 61, 159-162.
http://dx.doi.org/10.1071/CH07316

[15]. Aplander, K.; Hidestal, O.; Katebzadeh, K.; Lindstrom, U. M. A. Green Chem. 2006, 8, 22-24.
http://dx.doi.org/10.1039/B513656C

[16]. Gupta, M.; Paul, S.; Gupta, R. Current Sci. 2010, 99, 1341-1360.

[17]. Butler, R. N.; Coyne, A. G. Water. Chem. Rev. 2010, 110, 6302-63037.
http://dx.doi.org/10.1021/cr100162c

[18]. Kumaravel, K.; Vasuki, G. Curr. Org. Chem. 2009,13, 1820-1841.
http://dx.doi.org/10.2174/138527209789630514

[19]. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748.
http://dx.doi.org/10.1021/cr800448q

[20]. Moseley, J. D.; Kappe, C. O. Green Chem. 2011, 13, 794-806.
http://dx.doi.org/10.1039/c0gc00823k

[21]. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman. J. Tetrahedron 2001, 57, 9225-9283.

[22]. Kappe, C. O. Chem. Soc. Rev. 2008, 37, 1127-1139.
http://dx.doi.org/10.1039/b803001b

[23]. Sarrafi, Y.; Sadatshahabi, M.; Alimohammadi, K.; Tajbakhsh, M. Green Chem. 2011, 13, 2851-2858.
http://dx.doi.org/10.1039/c1gc15625j

[24]. Moseley, J. D.; Kappe, C. O. Green Chem. 2011, 13, 794-806.
http://dx.doi.org/10.1039/c0gc00823k

[25]. Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454-457.
http://dx.doi.org/10.1021/ol102784c

[26]. De, S.; Dutta, S.; Saha, B. Green Chem. 2011, 13, 2859-2868.
http://dx.doi.org/10.1039/c1gc15550d

[27]. Carvalho, L. C. R. E.; Fernandes.; Marques M. M. B. Chem. Eur. J. 2011, 17, 12544-12555.
http://dx.doi.org/10.1002/chem.201101508

[28]. Farruggia, G.; Iotti, S.; Lombardo, M. Marraccini C.; Sgarzi, M.; Trombini, C.; Zaccheroni, N. J. Org. Chem. 2010, 75, 6275-6278.
http://dx.doi.org/10.1021/jo101173t

[29]. Domling, A. Chem. Rev. 2006, 106, 17-89.
http://dx.doi.org/10.1021/cr0505728

[30]. Ramon, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602-1632.
http://dx.doi.org/10.1002/anie.200460548

[31]. Tietze, L. F.; Brasche, G.; Gericke, K. M. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006.

[32]. Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Org. Lett. 2007, 9, 4223-4226.
http://dx.doi.org/10.1021/ol7018357

[33]. Singh, S. P.; Parmar, S. S.; Raman, K. Chem. Rev. 1981, 81, 175-203.
http://dx.doi.org/10.1021/cr00042a003

[34]. Brown, F. C. Chem. Rev. 1961, 61, 463-521.
http://dx.doi.org/10.1021/cr60213a002

[35]. Shah, T. J.; Desai, V. A. Arkivoc 2007, 14, 218-228.

[36]. Murugan, R.; Anbazhagan, S.; Lingeshwaran, S.; Narayanan, S. Eur. J. Med. Chem. 2009, 44, 3272-3279.
http://dx.doi.org/10.1016/j.ejmech.2009.03.035

[37]. Solomon, V. R.; Haq, W.; Srivastava, K.; Puri, S. K.; Katti, S. B. J. Med. Chem. 2007, 50, 394-398.
http://dx.doi.org/10.1021/jm061002i

[38]. Petrikaite, V.; Tarasevicius, E.; Pavilonis, A. Medicina (Kaunas) 2007, 43, 657-663.

[39]. Sortino, M.; Delgado, P.; Juarez, S.; Quiroga, J.; Abonia, R.; Insuasty, B.; Nogueras, M.; Rodero, L.; Garibotto, F. M.; Enriz, R. D.; Zacchino, S. A. Bioorg. Med. Chem. 2007, 15, 484-494.
http://dx.doi.org/10.1016/j.bmc.2006.09.038

[40]. Kumar, A.; Sharma, S.; Archana, A.; Bajaj, K.; Sharma, S.; Panwar, H.; Singh, T.; Srivastava, V. K. Bioorg. Med. Chem. 2003, 11, 5293-5299.
http://dx.doi.org/10.1016/S0968-0896(03)00501-7

[41]. Sharma, S.; Singh, T.; Mittal, R.; Saxena, K. K.; Srivastava, V. K.; Kumar, A. Arch. Pharm. Chem. Life Sci. 2006, 339, 145-152.
http://dx.doi.org/10.1002/ardp.200500215

[42]. Brooke, E. W.; Davies, S. G.; Mulvaney, A. W.; Okada, M.; Pompeo, F.; Sim, E.; Vickers, R. J.; Westwood, I. M. Bioorg. Med. Chem. 2003, 13, 2527-2530.
http://dx.doi.org/10.1016/S0960-894X(03)00484-0

[43]. Surender, S. J.; Barij, N. S.; Rolf, H.; Boris, P.; Xavier, L.; Venkatesan, J. Eur. J. Med. Chem. 2015, 89(7), 172-178.

[44]. Mallikarjuna, B. P.; Sastry, B. S.; Suresh, K. G. V.; Rajendraprasad, Y.; Chandrashekar, S. M.; Sathisha, K. Eur. J. Med. Chem. 2009, 44, 4739-4746.
http://dx.doi.org/10.1016/j.ejmech.2009.06.008

[45]. Rawal, R. K.; Tripathi, R.; Katti, S. B.; Pannecouque, C.; Clercq, E. D. Eur. J. Med. Chem. 2008, 43, 2800-2806.
http://dx.doi.org/10.1016/j.ejmech.2007.12.015

[46]. Andreas, P. L.; Carmen, B. R.; Dieter, S.; Holger, S.; Bettina, H. Eur. J. Med. Chem. 2015, 89(7), 503-523.

[47]. Chandrappa, S.; Kavitha, C. V.; Shahabuddin, M. S.; Vinaya, K.; Ananda, C. S.; Ranganatha, S. R.; Raghavan, S. C.; Rangappa, K. S. Bioorg. Med. Chem. 2009, 17, 2576-2584.
http://dx.doi.org/10.1016/j.bmc.2009.01.016

[48]. Roman, L.; Boris, Z.; Ivanna, S.; Igor, N.; Gennadij, K. Acta Pol. Pharm-Drug. Res. 2003, 6, 457-466.

[49]. Vachal, P.; Pihera, P.; Svoboda, J. Chem. Commun. 1997, 62, 1468-1480.

[50]. Lesyk, R.; Zimenkovsky, B.; Subtelna, I.; Nektegayev, I.; Kazmirchuk, G. Acta. Pol. Pharm. Drug-Res. 2003, 6, 457-466.

[51]. Lesyk, R. B.; Zimenkovsky, B. S. Curr. Org. Chem. 2004, 8, 1547-1577.
http://dx.doi.org/10.2174/1385272043369773

[52]. Marko, R.; Botta, L.; Gianni, C.; Martino, B.; Botta, M. J. Comb. Chem. 2010, 12, 200-205.
http://dx.doi.org/10.1021/cc9001789

[53]. Taylor, E. C.; Lee, H. H. J. Am. Chem. Soc. 1954, 76, 1870-1872.
http://dx.doi.org/10.1021/ja01636a039

[54]. Hu, B.; Malamas, M.; Ellingboe, J.; Largis, E.; Han, S.; Mulvey, R.; Tillett, J. Bioorg. Med. Chem. Lett. 2001, 11, 981-984.
http://dx.doi.org/10.1016/S0960-894X(01)00147-0

[55]. Pulici, M.; Tetrahedron Lett. 2005, 46, 2387-2391.
http://dx.doi.org/10.1016/j.tetlet.2005.02.059

[56]. Pansare, D.; Shinde, D. B. Tetrahedron Lett. 2014, 55, 1107-1110.
http://dx.doi.org/10.1016/j.tetlet.2013.12.113

[57]. Simpson, J.; Rathbone, D.; Billington D. C. Tetrahedron Lett. 1999, 40, 7031-7033.
http://dx.doi.org/10.1016/S0040-4039(99)01448-3

[58]. Jadhav, S. A.; Shioorkar, M. G.; Chavan, O. S. Shinde, D. B.; Pardeshi, R. K. Heterocyclic Lett. 2015, 5, 3, 375-382.

[59]. Jadhav, S. A.; Shioorkar, M. G.; Chavan, O. S.; Pardeshi, R. K. S. Der Pharma Chemica 2015, 7(2), 127-131.

[60]. Jadhav, S. A.; Shioorkar, M. G.; Chavan, O. S.; Chavan, R.; Shinde, D. B.; Pardeshi, R. K. Der Pharma Chemica 2015, 7(5), 329-334.

[61]. Shioorkar, M. G.; Ubale, M. B. Jadhav, S. A.; Pardeshi, R. K. Der Chemica Sinica 2015, 6(4), 110-113.

[62]. Omprakash, S. C.; Chavan, S. B.; Jadhav, S. A.; Shioorkar, M. G.; Baseer, M. A. Heterocyclic Lett. 2015, 5(3), 391-394.

[63]. Santosh, A. J.; Mahesh, G. S.; Omprakash, S. C.; Aniket, P. S.; Devanand, B. S.; Rajendra, K. P. Chem. Mater. Res. 2015, 7(8), 106-111.

Supporting Agencies

Principal and Head, Department of Chemistry, Sant Ramdas College, Ghansawangi, Dist. Jalna affiliated to Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 (MS), India
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).