European Journal of Chemistry 2015, 6(4), 410-416 | doi: https://doi.org/10.5155/eurjchem.6.4.410-416.1312 | Get rights and content

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


Santosh Jadhav (1) , Mahesh Shioorkar (2) , Omprakash Chavan (3) , Aniket Sarkate (4) , Devanand Shinde (5) , Rajendra Pardeshi (6,*)

(1) Department of Chemistry, Vivekanand College, Aurangabad, MS, 431001, India
(2) Department of Chemistry, Vivekanand College, Aurangabad, MS, 431001, India
(3) Department of Chemistry, Barwale College, Jalna, MS, 431203, India
(4) Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431001, India
(5) Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431001, India
(6) Department of Chemistry, Sant Ramdas College, Ghansawangi, Jalna, MS, 431203, India
(*) Corresponding Author

Received: 22 Aug 2015 | Revised: 14 Sep 2015 | Accepted: 19 Sep 2015 | Published: 31 Dec 2015 | Issue Date: December 2015

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.


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Keywords


Alum; Water; Aldehyde; Rhodanine; Triethyl amine; Microwave-assisted synthesis

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DOI: 10.5155/eurjchem.6.4.410-416.1312

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Funding information


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

Citations

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[2]. Goutam Brahmachari, Khondekar Nurjamal, Sanchari Begam, Mullicka Mandal, Nayana Nayek, Indrajit Karmakar, Bhagirath Mandal
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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.


How to cite


Jadhav, S.; Shioorkar, M.; Chavan, O.; Sarkate, A.; Shinde, D.; Pardeshi, R. Eur. J. Chem. 2015, 6(4), 410-416. doi:10.5155/eurjchem.6.4.410-416.1312
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(4), 410-416. doi:10.5155/eurjchem.6.4.410-416.1312
Jadhav, S., Shioorkar, M., Chavan, O., Sarkate, A., Shinde, D., & Pardeshi, R. (2015). Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water. European Journal of Chemistry, 6(4), 410-416. doi:10.5155/eurjchem.6.4.410-416.1312
Jadhav, Santosh, Mahesh Shioorkar, Omprakash Chavan, Aniket Sarkate, Devanand Shinde, & Rajendra Pardeshi. "Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water." European Journal of Chemistry [Online], 6.4 (2015): 410-416. Web. 3 Jun. 2023
Jadhav, Santosh, Shioorkar, Mahesh, Chavan, Omprakash, Sarkate, Aniket, Shinde, Devanand, AND Pardeshi, Rajendra. "Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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