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






  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


Keywords


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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.1.4.377-380.165

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1388 times | PDF Article downloaded 392 times


Citations

/


[1]. 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
/


[2]. 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
/


[3]. 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
/


[4]. 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
/


[5]. 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
/


[6]. 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
/


[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(2 H )-ones
Tetrahedron  69(17), 3530, 2013
DOI: 10.1016/j.tet.2013.02.093
/


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


[9]. 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
/


[10]. 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
/


[11]. 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
/


[12]. 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
/


[13]. 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
/


[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]. 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
/


[16]. 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
/


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


[18]. 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
/


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. 27 Jan. 2020
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)

DOI Link: https://doi.org/10.5155/eurjchem.1.4.377-380.165

| | | | |

| | | | | |

Save to Zotero Save 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 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort