Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Letter Article

[bmim]BF4-accelarated One-pot Synthesis of 2-amino Thiazole Derivatives

Author(s): Dau Xuan Duc* and Nguyen Thi Chung

Volume 20, Issue 8, 2023

Published on: 01 March, 2023

Page: [689 - 695] Pages: 7

DOI: 10.2174/1570178620666230207093953

Price: $65

conference banner
Abstract

An efficient and environmentally-friendly protocol for the synthesis of 2- (arylamino) thiazoles has been investigated. The two-step, three-component reaction of aryl ketones, Nbromosuccinimide, and thiourea derivatives was performed using [bmim][BF4] ionic liquid as a solvent in one pot and gave products in good to excellent yields. Furthermore, the ionic liquid could be reused up to the 5th time without a considerable decrease in the reaction yield. Thirteen thiazoles were obtained in high yields (78-89%) under mild conditions (ambient temperature and relatively short reaction time) and their structures were confirmed by NMR data.

Next »
Graphical Abstract

[1]
Duc, D.X.; Chung, N.T. Curr. Org. Synth., 2022, 19(6), 702-730.
[http://dx.doi.org/10.2174/1570179419666220216122637] [PMID: 35170413]
[2]
Pratt, J.; Jae, H.S.; Rosenberg, S.; Spina, K.; Winn, M.; Buckner, S.; Novosad, E.; Kerkman, D.; Shiosaki, K.; Opgenorth, T.; DeBernardis, H. Bioorg. Med. Chem. Lett., 1994, 4(1), 169-172.
[http://dx.doi.org/10.1016/S0960-894X(01)81141-0]
[3]
Langille, N.F.; Dakin, L.A.; Panek, J.S. Org. Lett., 2002, 4(15), 2485-2488.
[http://dx.doi.org/10.1021/ol026099r] [PMID: 12123357]
[4]
Bulut, I.; Chávez, P.; Mirloup, A.; Huaulmé, Q.; Hébraud, A.; Heinrich, B.; Fall, S.; Méry, S.; Ziessel, R.; Heiser, T.; Lévêque, P.; Leclerc, N. J. Mater. Chem. C Mater. Opt. Electron. Devices, 2016, 4(19), 4296-4303.
[http://dx.doi.org/10.1039/C6TC00531D]
[5]
Lin, Y.; Fan, H.; Li, Y.; Zhan, X. Adv. Mater., 2012, 24(23), 3087-3106, 3081.
[http://dx.doi.org/10.1002/adma.201200721] [PMID: 22581766]
[6]
Ando, S.; Murakami, R.; Nishida, J.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. J. Am. Chem. Soc., 2005, 127(43), 14996-14997.
[http://dx.doi.org/10.1021/ja055686f] [PMID: 16248617]
[7]
Paul, M.; Sudkaow, P.; Wessels, A.; Schlörer, N.E.; Neudörfl, J.M.; Berkessel, A. Angew. Chem. Int. Ed., 2018, 57(27), 8310-8315.
[http://dx.doi.org/10.1002/anie.201801676] [PMID: 29645334]
[8]
Fink, B.E.; Mortensen, D.S.; Stauffer, S.R.; Aron, Z.D.; Katzenellenbogen, J.A. Chem. Biol., 1999, 6(4), 205-219.
[http://dx.doi.org/10.1016/S1074-5521(99)80037-4] [PMID: 10099132]
[9]
Potewar, T.M.; Ingale, S.A.; Srinivasan, K.V. Tetrahedron, 2007, 63(45), 11066-11069.
[http://dx.doi.org/10.1016/j.tet.2007.08.036]
[10]
Benzekri, Z.; Serrar, H.; Sibous, S.; Boukhris, S.; Ouasri, A.; Rhandour, A.; Souizi, A. Green Chem. Lett. Rev., 2016, 9(4), 223-228.
[http://dx.doi.org/10.1080/17518253.2016.1242662]
[11]
Izumisawa, Y.; Togo, H. Green Sustain. Chem, 2011, 1, 54-62.
[12]
Yavari, I.; Sayyed-Alangi, S.Z.; Hajinasiri, R.; Sajjadi-Ghotbabadi, H. Monatsh. Chem., 2009, 140(2), 209-211.
[http://dx.doi.org/10.1007/s00706-008-0065-7]
[13]
Lingampalle, D.L.; Mane, R.A. Pharma Chem., 2017, 9, 147-149.
[14]
Muthyala, M.K.; Kumar, A. J. Heterocycl. Chem., 2012, 49(4), 959-964.
[http://dx.doi.org/10.1002/jhet.904]
[15]
Vražič, D.; Jereb, M.; Laali, K.; Stavber, S. Molecules, 2012, 18(1), 74-96.
[http://dx.doi.org/10.3390/molecules18010074] [PMID: 23344189]
[16]
Jawale, D.V.; Lingampalle, D.L.; Pratap, U.R.; Mane, R.A. Chin. Chem. Lett., 2010, 21(4), 412-416.
[http://dx.doi.org/10.1016/j.cclet.2009.11.035]
[17]
Kidwai, M.; Bhatnagar, D.; Mothsra, P.; Singh, A.K.; Dey, S. J. Sulfur Chem., 2009, 30(1), 29-36.
[http://dx.doi.org/10.1080/17415990802422365]
[18]
Potewar, T.M.; Ingale, S.A.; Srinivasan, K.V. Tetrahedron, 2008, 64(22), 5019-5022.
[http://dx.doi.org/10.1016/j.tet.2008.03.082]
[19]
Banothu, J.; Vaarla, K.; Bavantula, R.; Crooks, P.A. Chin. Chem. Lett., 2014, 25(1), 172-175.
[http://dx.doi.org/10.1016/j.cclet.2013.10.001]
[20]
Rostamizadeh, S.; Aryan, R.; Ghaieni, H.R.; Amani, A.M. Monatsh. Chem., 2008, 139(10), 1241-1245.
[http://dx.doi.org/10.1007/s00706-008-0906-4]
[21]
Zhao, D.; Guo, S.; Guo, X.; Zhang, G.; Yu, Y. Tetrahedron, 2016, 72(35), 5285-5289.
[http://dx.doi.org/10.1016/j.tet.2016.05.010]
[22]
Kidwai, M.; Chauhan, R.; Bhatnagar, D. J. Sulfur Chem., 2011, 32(1), 37-44.
[http://dx.doi.org/10.1080/17415993.2010.533773]
[23]
Madhav, B.; Narayana Murthy, S.; Anil Kumar, B.S.P.; Ramesh, K.; Nageswar, Y.V.D. Tetrahedron Lett., 2012, 53(30), 3835-3838.
[http://dx.doi.org/10.1016/j.tetlet.2012.04.097]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy