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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | SHORT COMMUNICATION | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives


Behrooz Maleki (1,*) , Hafezeh Salehabadi (2)

(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.

1_4_377_380_800


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


2-Arylbenzothiazoles; Bisbenzothiazole; Aldehydes; Ammonium chloride; 2-Aminothiophenol; Mild condition

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.1.4.377-380.165

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 3159 times | icon graph PDF Article downloaded 895 times


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]. Ankush Mahajan, Monika Gupta
PolyVinyl alcohol and copper nickel co‐doped titania nanocomposite: Designing, characterization, optical properties, and catalytic application in the synthesis of aryl derivatives of benzothiazole and benzimidazole
Applied Organometallic Chemistry  37(10), , 2023
DOI: 10.1002/aoc.7195
/


[5]. 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
/


[6]. 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
/


[7]. 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
/


[8]. 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
/


[9]. 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
/


[10]. 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
/


[11]. 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
/


[12]. 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
/


[13]. 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
/


[14]. 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
/


[15]. 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
/


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


[17]. 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
/


[18]. Ranjeet Kumar Yadav, Rajnish Kumar, Himanshu Singh, Avijit Mazumdar, Salahuddin, Bharti Chauhan, Mohd. Mustaqeem Abdullah
Recent Insights on Synthetic Methods and Pharmacological Potential in Relation with Structure of Benzothiazoles
Medicinal Chemistry  19(4), 325, 2023
DOI: 10.2174/1573406418666220820110551
/


[19]. 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
/


[20]. 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
/


[21]. 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
/


[22]. 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
/


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


[24]. 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
/


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


[26]. 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
/


[27]. 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
/


[28]. 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
/


[29]. 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
/


[30]. 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
/


[31]. Ramesh Gawade, Pramod Kulkarni
DBUHI3 complex an efficient catalyst for the synthesis of 2-phenyl benzimidazole and benzothiazole derivatives
Journal of the Serbian Chemical Society  88(10), 959, 2023
DOI: 10.2298/JSC220526007G
/


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


Maleki, B.; Salehabadi, H. Eur. J. Chem. 2010, 1(4), 377-380. doi:10.5155/eurjchem.1.4.377-380.165
Maleki, B.; Salehabadi, H. Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives. Eur. J. Chem. 2010, 1(4), 377-380. doi:10.5155/eurjchem.1.4.377-380.165
Maleki, B., & Salehabadi, H. (2010). Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives. European Journal of Chemistry, 1(4), 377-380. doi:10.5155/eurjchem.1.4.377-380.165
Maleki, Behrooz, & Hafezeh Salehabadi. "Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives." European Journal of Chemistry [Online], 1.4 (2010): 377-380. Web. 30 Nov. 2023
Maleki, Behrooz, AND Salehabadi, Hafezeh. "Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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.