

Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water
Santosh Jadhav (1)






(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.
Announcements
One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.6.4.410-416.1312
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


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
[1]. A.M. Abdulwahab, Khadijah Mohammad AL-Dhabyani, Abdullah Ahmed Ali Ahmed, Naif Mohammed Al-Hada, A.A. Qaid
The effect of lithium doping on structural, thermal, optical and electrical properties of potash alum single crystals
Inorganic Chemistry Communications 145, 109985, 2022
DOI: 10.1016/j.inoche.2022.109985

[2]. Goutam Brahmachari, Khondekar Nurjamal, Sanchari Begam, Mullicka Mandal, Nayana Nayek, Indrajit Karmakar, Bhagirath Mandal
Alum (KAl(SO4)2.12H2O) - An Eco-friendly and Versatile Acid-catalyst in Organic Transformations: A Recent Update
Current Green Chemistry 6(1), 12, 2019
DOI: 10.2174/2213346106666190307160332

[3]. Manar G. Salem, Yasmine M. Abdel Aziz, Marwa Elewa, Mohamed S. Nafie, Hosam A. Elshihawy, Mohamed M. Said
Synthesis, molecular modeling, selective aldose reductase inhibition and hypoglycemic activity of novel meglitinides
Bioorganic Chemistry 111, 104909, 2021
DOI: 10.1016/j.bioorg.2021.104909

[4]. Nisheeth C. Desai, Yogesh M. Rupala, Ashvinkumar G. Khasiya, Keyur N. Shah, Unnat P. Pandit, Vijay M. Khedkar
Synthesis, biological evaluation, and molecular docking study of thiophene‐, piperazine‐, and thiazolidinone‐based hybrids as potential antimicrobial agents
Journal of Heterocyclic Chemistry 59(1), 75, 2022
DOI: 10.1002/jhet.4366

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
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.6.4.410-416.1312

















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
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.