

Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives
Behrooz Maleki (1,*)


(1) Department of Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar, IR-397, Iran
(2) Department of Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar, IR-397, Iran
(*) Corresponding Author
Received: 14 Jun 2010 | Revised: 02 Oct 2010 | Accepted: 28 Oct 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
An efficient protocol has been developed for the preparation of a series of 2-arylbenzothiazoles derivatives from condensation of 2-aminothiophenol with aromatic aldehydes using ammonium chloride, which is a very inexpensive, metal-free and readily available reagent. The target compounds were obtained in good to excellent yields (58-92%) under fairly mild reaction conditions at room temperature.
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.1.4.377-380.165
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Tanzeela Qadir, Andleeb Amin, Alka Salhotra, Praveen Kumar Sharma, Ishtiaq Jeelani, Hitoshi Abe
Recent Advances in the Synthesis of Benzothiazole and its Derivatives
Current Organic Chemistry 26(2), 189, 2022
DOI: 10.2174/1385272826666211229144446

[2]. Gurpreet Kaur, Radha Moudgil, Mussarat Shamim, Vivek Kumar Gupta, Bubun Banerjee
Camphor sulfonic acid catalyzed a simple, facile, and general method for the synthesis of 2-arylbenzothiazoles, 2-arylbenzimidazoles, and 3H-spiro[benzo[d]thiazole-2,3′-indolin]-2′-ones at room temperature
Synthetic Communications 51(7), 1100, 2021
DOI: 10.1080/00397911.2020.1870043

[3]. Hiroyoshi Ohtsu, Wanuk Choi, Nazrul Islam, Yoshitaka Matsushita, Masaki Kawano
Selective Trapping of Labile S3 in a Porous Coordination Network and the Direct X-ray Observation
Journal of the American Chemical Society 135(31), 11449, 2013
DOI: 10.1021/ja4046718

[4]. Sachin P. Gadekar, Machhindra K. Lande
Ruthenium silicate (RS-1) zeolite: novel heterogeneous efficient catalyst for synthesis of 2-arylbenzothiazole derivatives
Research on Chemical Intermediates 47(3), 1253, 2021
DOI: 10.1007/s11164-020-04353-y

[5]. Sudipto Das, Suvendu Samanta, Swarup Kumar Maji, Partha Kumar Samanta, Amit Kumar Dutta, Divesh N. Srivastava, Bibhutosh Adhikary, Papu Biswas
Visible-light-driven synthesis of 2-substituted benzothiazoles using CdS nanosphere as heterogenous recyclable catalyst
Tetrahedron Letters 54(9), 1090, 2013
DOI: 10.1016/j.tetlet.2012.12.044

[6]. Gi Hyeon Sung, In-Hye Lee, Bo Ram Kim, Dong-Soo Shin, Jeum-Jong Kim, Sang-Gyeong Lee, Yong-Jin Yoon
Eco-friendly atom-economical synthesis of 2-substituted-benzo[d]thiazoles and 2-substituted-benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones
Tetrahedron 69(17), 3530, 2013
DOI: 10.1016/j.tet.2013.02.093

[7]. Hossa F. Al-Shareef, Heba A. Elhady, Amany H. Aboellil, Essam M. Hussein
Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities
SpringerPlus 5(1), , 2016
DOI: 10.1186/s40064-016-2458-0

[8]. Thaksen Jadhav, Bhausaheb Dhokale, Shaikh M. Mobin, Rajneesh Misra
Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation
RSC Advances 5(38), 29878, 2015
DOI: 10.1039/C5RA04881H

[9]. Xiang Gao, Jiao Liu, Xin Zuo, Xinyue Feng, Ying Gao
Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry
Molecules 25(7), 1675, 2020
DOI: 10.3390/molecules25071675

[10]. Arup Datta
Pentafluorophenylammonium triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
Oriental Journal Of Chemistry 37(1), 95, 2021
DOI: 10.13005/ojc/370112

[11]. Bimal B. Chakraborty, Siddique Anwar, Saurav Das, Satya B. Paul, Golam Mohiuddin, Joydip De, Sudip Choudhury
Aggregation dependent fluorescence switching in benzothiazole derivative based H-bonded mesogen
Liquid Crystals 45(11), 1644, 2018
DOI: 10.1080/02678292.2018.1468499

[12]. Anupama Ekbote, Shaikh M. Mobin, Rajneesh Misra
Stimuli-responsive phenothiazine-based donor–acceptor isomers: AIE, mechanochromism and polymorphism
Journal of Materials Chemistry C 8(10), 3589, 2020
DOI: 10.1039/C9TC05192A

[13]. Zhi-Yu Yu, Qiu-Sheng Fang, Jia Zhou, Zhi-Bin Song
Reusable proline-based ionic liquid catalyst for the simple synthesis of 2-arylbenzothiazoles in a biomass medium
Research on Chemical Intermediates 42(3), 2035, 2016
DOI: 10.1007/s11164-015-2133-z

[14]. Nuaman F. Alheety, Leqaa A. Mohammed, Abdulwahhab H. Majeed, Shankar Sehgal, Bilal J.M. Aldahham, Mustafa A. Alheety
The effect of addition Ag and MnO2 nanoparticles in the hydrogen storage of ethyl 2-((5-methoxybenzo[d]thiazol-2-yl)thio)acetate (organic: Inorganic nanohybrids)
Journal of the Indian Chemical Society 99(10), 100734, 2022
DOI: 10.1016/j.jics.2022.100734

[15]. Hiroyoshi Ohtsu, Masaki Kawano
Kinetic assembly of coordination networks
Chemical Communications 53(63), 8818, 2017
DOI: 10.1039/C7CC04277A

[16]. Anupama Ekbote, Shaikh M. Mobin, Rajneesh Misra
Structure–property relationship in multi-stimuli responsive D–A–A′ benzothiazole functionalized isomers
Journal of Materials Chemistry C 6(40), 10888, 2018
DOI: 10.1039/C8TC04310H

[17]. Arash Shokrolahi, Abbas Zali, Mohammd Mahdavi
Sulfonated Porous Carbon (SPC)-Catalyzed Synthesis of Benzothiazole Derivatives in Water
Phosphorus, Sulfur, and Silicon and the Related Elements 187(4), 535, 2012
DOI: 10.1080/10426507.2011.631642

[18]. Neelam P. Prajapati, Rajesh H. Vekariya, Mayuri A. Borad, Hitesh D. Patel
Recent advances in the synthesis of 2-substituted benzothiazoles: a review
RSC Adv. 4(104), 60176, 2014
DOI: 10.1039/C4RA07437H

[19]. Xing Liu, Zhi-Bing Dong
A Review on Domino Condensation/Cyclization Reactions for the Synthesis of 2-Substituted 1,3-Benzothiazole Derivatives
European Journal of Organic Chemistry 2020(4), 408, 2020
DOI: 10.1002/ejoc.201901502

[20]. L. M. Pevzner, A. I. Ponyaev
Phosphonomethylated Acetoxymethyl Derivatives of Acetylfurans and Alkyl Furoates with the Remote Location of Substituents: Synthesis and Further Transformations
Russian Journal of General Chemistry 93(3), 513, 2023
DOI: 10.1134/S1070363223030088

[21]. Smita R. Waghmare
NH4Cl Catalyzed synthesis of β-amino Esters
Results in Chemistry 2, 100036, 2020
DOI: 10.1016/j.rechem.2020.100036

[22]. Batchu Chandrasekhar
2-Alkyl/aryl/heteroarylbenzothiazole ring systems fromo-aminothiophenol and its derivatives as versatile synthons
Journal of Sulfur Chemistry 35(5), 538, 2014
DOI: 10.1080/17415993.2014.934245

[23]. Deepak Devadiga, T. N. Ahipa
Recent synthetic advances in pyridine-based thermotropic mesogens
RSC Advances 9(40), 23161, 2019
DOI: 10.1039/C9RA04389F

[24]. Sh. A. Abdel-Mohsen, E. M. Hussein
A green synthetic approach to the synthesis of Schiff bases from 4-amino-2-thioxo-1,3-diazaspiro[5.5]undec-4-ene-5-carbonitrile as potential anti-inflammatory agents
Russian Journal of Bioorganic Chemistry 40(3), 343, 2014
DOI: 10.1134/S1068162014030029

[25]. Salman Rahmani, Ali Amoozadeh, Eskandar Kolvari
Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
Catalysis Communications 56, 184, 2014
DOI: 10.1016/j.catcom.2014.07.002

[26]. Xiaowei Li, Yuxiu Li, Ruihua Liu, Zemin Wang, Xiangqian Li, Dayong Shi
AcOH-mediated aerobic oxidative synthesis of 2-thioalkylbenzothiazoles via a three-component reaction
Tetrahedron Letters 61(26), 152054, 2020
DOI: 10.1016/j.tetlet.2020.152054

[27]. E. M. Hussein
Ammonium chloride-catalyzed four-component sonochemical synthesis of novel hexahydroquinolines bearing a sulfonamide moiety
Russian Journal of Organic Chemistry 51(1), 54, 2015
DOI: 10.1134/S1070428015010091

[28]. Ali Amoozadeh, Rahmat Allah Azadeh, Salman Rahmani, Mehdi Salehi, Maciej Kubicki, Grzegorz Dutkiewicz
Nano-Titania-Supported Sulfonic-Acid-Catalyzed Synthesis of 2-Arylbenzothiazole Derivatives Under Solvent Free Conditions
Phosphorus, Sulfur, and Silicon and the Related Elements 190(11), 1874, 2015
DOI: 10.1080/10426507.2015.1031753

References
[1]. Hays, S.; Rice, J. M. J.; Ortwine, D. F.; Johnson, G.; Schwarz, R. D.; Boyd, D. K.; Copeland, L. F.; Vartanian, M. G.; Boxer, P. A. J. Pharm. Sci. 1994, 83, 1425-1432.
doi:10.1002/jps.2600831013
PMid:7884664
[2]. Hotchinson, I.; Chua, M. S.; Browne, H. L.; Trapani, V. J. Med. Chem. 2001, 44, 1446-1455.
doi:10.1021/jm001104n
PMid:11311068
[3]. Mathis, C. A.; Wang, Y.; Holt, D. P.; Huang, G. F.; Debnath, M. L.; Klunk, W. E. J. Med. Chem. 2003, 46, 2740-2754.
doi:10.1021/jm030026b
PMid:12801237
[4]. Sharghi, H.; Omid, A. Synth. Commun. 2009, 39, 860-867.
doi:10.1080/00397910802431214
[5]. Paul, S.; Gupta, M.; Gupta, R. Synth. Commun. 2002, 32, 3541-3547.
doi:10.1081/SCC-120014964
[6]. Nadaf, R. N.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Mol. Catal. A: Chem. 2004, 214, 155-160.
doi:10.1016/j.molcata.2003.10.064
[7]. Matsushita, H.; Lee, S. H.; Joung, M.; Clapham, B.; Janda, K. D. Tetrahedron Lett. 2004, 45, 313-316.
doi:10.1016/j.tetlet.2003.10.168
[8]. Alagile, D.; Baldwin, R. M.; Tamagnan, G. D. Tetrahedron Lett. 2005, 46, 1349-1351.
doi:10.1016/j.tetlet.2004.12.111
[9]. Chen, C.; Chen, Y. J. Tetrahedron Lett. 2004, 45, 113-115.
doi:10.1016/j.tetlet.2003.10.095
[10]. Majo, V. J.; Prabhakaran, J.; Mann, J. J.; Kumar, J. S. D. Tetrahedron Lett. 2003, 44, 8535-8537.
doi:10.1016/j.tetlet.2003.09.138
[11]. Bougrin, K.; Loupy, A.; Soufiaoui, M. Tetrahedron 1998, 45, 8055-8064.
doi:10.1016/S0040-4020(98)00431-1
[12]. Rostamizadeh, S.; Housaini, K. S. A. Phosphrus Sulfur Silicon Relat. Elem. 2003, 180, 1321-1326.
doi:10.1080/10426500590912268
[13]. Li, Y.; Wang, G. Y.; Wang, J. Y.; Jacquline, L. Chem. Lett. 2006, 35, 460-461.
doi:10.1246/cl.2006.460
[14]. Ranu, B. C.; Jana, R.; Dey, S. Chem. Lett. 2004, 33, 274-275.
doi:10.1246/cl.2004.274
[15]. Kawashita, Y.; Ueba, C.; Hayashi, M. Tetrahedron Lett. 2006, 47, 4231-4233.
doi:10.1016/j.tetlet.2006.04.019
[16]. Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles 2004, 62, 197-201.
doi:10.3987/COM-03-S(P)47
[17]. Al-Qalaf, F.; Mekheimer, R. R.; Sadek, K. U. Molecules 2008, 13, 2908-2914.
doi:10.3390/molecules13112908
PMid:19037182
[18]. Okimoto, M.; Yoshida, T.; Hoshi, M.; Hottori, K.; Komata, M.; Tomozawa, K.; Chiba, T. Heterocycles 2008, 75, 35-42.
doi:10.3987/COM-07-11195
[19]. Chanada, M.; Arup, D. A. Heterocycles 2007, 71, 1837-1842.
doi:10.3987/COM-07-11079
[20]. Makhopadhyay, C.; Datta, A. J. Het. Chem. 2009, 46, 91-95.
doi:10.1002/jhet.9
[21]. Bahrami, K.; Khodaei, M. M.; Naali, F. Synlett 2009, 4, 569-572.
doi:10.1055/s-0028-1087911
[22]. Fazaeli, R.; Aliyan, H. Appl. Catal. A: Gen. 2009, 353, 74-79.
doi:10.1016/j.apcata.2008.10.035
[23]. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Aust. J. Chem. 2008, 61, 905-909.
doi:10.1071/CH08122
[24]. Pratap, U. R.; Mali, J. R.; Jawale, D. V.; Mane, R. A. Tetrahedron Lett. 2009, 50, 1352-1354.
doi:10.1016/j.tetlet.2009.01.032
[25]. Xiao, H. L.; Chen, J. X.; Liu, M. C.; Zhu, D. J.; Ding, J. C.; Wu, H. Y. Chem. Lett. 2009, 38, 170-171.
doi:10.1246/cl.2009.170
[26]. Abdollahi-Alibeik, M.; Poorirani, S. Phosphorus Sulfur Silicon Relat. Elem. 2009, 184, 3182-3190.
doi:10.1080/10426500802705453
[27]. Aliyan, A.; Fazlaeli, R.; Fazaeli, N.; Mssah, A. R.; Javaherian-Naghash, H.; Alizadeh, M.; Emami, G. Heteroatom Chem. 2009, 4, 202-207.
doi:10.1002/hc.20534
[28]. Ralls, J. W.; Lundin, R. E.; Bailleg, G. F. J. Org. Chem. 1963, 28, 3521-3526.
doi:10.1021/jo01047a061
[29]. Shaabani, A.; Bazgir, A.; Thimouri, F. Tetrahedron Lett. 2003, 44, 857-859.
doi:10.1016/S0040-4039(02)02612-6
[30]. Chen, W. G.; Shi, L. Catal. Commun. 2008, 9, 1079-1081.
doi:10.1016/j.catcom.2007.10.011
[31]. Azizian, J.; Thimouri, F.; Mohammadizadeh, F. M. Catal. Commun. 2007, 8, 1117-1121.
doi:10.1016/j.catcom.2006.06.002
[32]. Darabi, H. R.; Tahoori, F.; Aghapoor, K.; Taala, F.; Mohsenzaeh, F. J. Brazil. Chem. Soc. 2008, 19, 1646-1652.
[33]. Azarifar, D.; Maleki, B.; Setayeshnazar, M. Phosphrus Sulfur Silicon Relat. Elem. 2009, 184, 2097-2102.
doi:10.1080/10426500802423933
[34]. Maleki, B.; Azarifar, D.; Hojati, S. F.; Gholizadeh, M.; Veisi, H.; Salehabadi, H.; Khodaverdian Moghadam, M. J. Het. Chem. 2011, DOI: 10.1002/jhet.426, in press.
[35]. Maleki, B.; Salehabadi, H.; Khodaverdian-Moghadam, M. Acta Chim. Slov. 2010, 3, 741-745.
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.1.4.377-380.165

















European Journal of Chemistry 2010, 1(4), 377-380 | doi: https://doi.org/10.5155/eurjchem.1.4.377-380.165 | 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.