European Journal of Chemistry 2010, 1(1), 33-36 | doi: https://doi.org/10.5155/eurjchem.1.1.33-36.5 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis of some novel Schiff bases containing 1,2,4-triazole ring


Akbar Mobinikhaledi (1,*) , Naser Foroughifar (2) , Mansooreh Khanpour (3) , Sattar Ebrahimi (4)

(1) Department of Chemistry, Faculty of Sciences, Arak University, Arak, IR-38156, Iran
(2) Department of Chemistry, Faculty of Sciences, Arak University, Arak, IR-38156, Iran
(3) Department of Chemistry, Faculty of Sciences, Arak University, Arak, IR-38156, Iran
(4) Department of Chemistry, Faculty of Sciences, Arak University, Arak, IR-38156, Iran
(*) Corresponding Author

Received: 24 Mar 2010 | Accepted: 24 Mar 2010 | Published: 31 Mar 2010 | Issue Date: March 2010

Abstract


4-Allyl-5-piridine-4-yl-4H-1,2,4-triazole-3-thiol was prepared under facile condition via the formation of 2-isonicotinoyl-N-allylhydrazinecarbothioamide. In addition, ethyl[(4-allyl-5-pyridine-4-yl-4H-1¸2¸4-triazole-3-yl)thio]acetate was synthesized via the reaction of 4-allyl-5-piridine-4-yl-4H-1,2,4-triazole-3-thiol with ethyl chloroacetate. 2-[(4-Allyl-5-pyridine-4-yl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide obtained by using ethyl[(4-allyl-5-pyridine-4-yl-4H-1¸2¸4-triazole-3-yl)thio]acetate as a precursor by two steps, was converted to Schiff base derivatives, 6a-j. All synthesized compounds were characterized by elemental analyses, IR spectroscopy, 1H NMR and 13C NMR spectroscopy. The cis/trans conformers of E isomer were present in DMSO solution of compounds 6a-j.

1_1_33_36_800


Keywords


1,2,4-triazole; Schiff bases; Acetohydrazide; Synthesis; Heterocyclic compounds

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.1.1.33-36.5

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 8786 times | PDF Article downloaded 812 times

Funding information


Research Council of Arak University

Citations

/


[1]. Naesr Foroughifar, Akbar Mobinikhaledi, Sattar Ebrahimi, Maryam Kamali, Maryam Kazemi
A simple and efficient procedure for synthesis of optically active 1,2-bis(s-triazolo (Bis (S-triazolo[3,4-b][1,3,4]thiadiazole-3-yl) alkane derivatives containingL-amino acid moieties
Journal of Sulfur Chemistry  32(6), 593, 2011
DOI: 10.1080/17415993.2011.628992
/


[2]. Akbar Mobinikhaledi, Mahsa Jabbarpour
Preparation, characterization, and biological activity of some new Schiff bases derived from aminophenoxy alkyloxy benzenamines and salicylaldehyde in the presence of p-TSA, and their Zn(II) and Cu(II) complexes
Research on Chemical Intermediates  41(2), 511, 2015
DOI: 10.1007/s11164-013-1205-1
/


[3]. Naesr Foroughifar, Sattar Ebrahimi, Akbar Mobinikhaledi, Reza Mozafari
An efficient and convenient protocol for the synthesis of optically active [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives containing L-amino acid moieties
Heterocyclic Communications  17(5-6), , 2011
DOI: 10.1515/HC.2011.048
/


[4]. Sattar Ebrahimi, Masoomeh Sayadi, Ghasem Darvishi
A simple and efficient procedure for the synthesis of optically active s-triazolothiadiazole derivatives
Chinese Chemical Letters  23(12), 1335, 2012
DOI: 10.1016/j.cclet.2012.10.014
/


[5]. Vitor F Ferreira, David R da Rocha, Fernando C da Silva, Patrícia G Ferreira, Núbia A Boechat, Jorge L Magalhães
Novel 1H-1,2,3-, 2H-1,2,3-, 1H-1,2,4- and 4H-1,2,4-triazole derivatives: a patent review (2008 – 2011)
Expert Opinion on Therapeutic Patents  23(3), 319, 2013
DOI: 10.1517/13543776.2013.749862
/


[6]. Sattar Ebrahimi
Synthesis of some pyridyl and cyclohexyl substituted 1,2,4 triazole, 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives
European Journal of Chemistry  1(4), 322, 2010
DOI: 10.5155/eurjchem.1.4.322-324.65
/


[7]. Deepak Lokwani, Rajaram Azad, Aniket Sarkate, Pallu Reddanna, Devanand Shinde
Structure Based Library Design (SBLD) for new 1,4-dihydropyrimidine scaffold as simultaneous COX-1/COX-2 and 5-LOX inhibitors
Bioorganic & Medicinal Chemistry  23(15), 4533, 2015
DOI: 10.1016/j.bmc.2015.06.008
/


[8]. Nadia Abdalla Khalil, Aliaa Moh Kamal, Soha Hussein Emam
Design, Synthesis, and Antitumor Activity of Novel 5-Pyridyl-1,3,4-oxadiazole Derivatives against the Breast Cancer Cell Line MCF-7
Biological & Pharmaceutical Bulletin  38(5), 763, 2015
DOI: 10.1248/bpb.b14-00867
/


[9]. Akbar Mobinikhaledi, Mojgan Zendehdel, Parvin Safari, Ahmad Hamta, S. Mehdi Shariatzadeh
Synthesis and Biological Activity Evaluation of Some Binuclear Metal Complexes of Cu(II) and Zn(II) with Tridentate Schiff Base Ligands
Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry  42(2), 165, 2012
DOI: 10.1080/15533174.2011.609512
/


[10]. Aeysha Sultan, Mian Habib Ur Rehman, Noreen Sajjad, Ali Irfan, Irfan Ullah, Muhammad Mustaqeem, Muhammad Saleem, Syeda Laila Rubab, Muhammad Rafiq, Muhammad Khalid, Katarzyna Kotwica-Mojzych, Mariusz Mojzych, Mohammad Shahid
A facile sonochemical protocol for synthesis of 3-amino- and 4-amino-1,2,4-triazole derived Schiff bases as potential antibacterial agents
PLOS ONE  15(6), e0229891, 2020
DOI: 10.1371/journal.pone.0229891
/


References

[1]. Unangst, P. C.; Shurum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. J. Med. Chem. 1992, 35, 3691-3698.
doi:10.1021/jm00098a015
PMid:1433181

[2]. Mullican, M. D.; Wilson, M. W.; Connor, D. T.; Kostlan, C. R.; Schrier, D. J.; Dyer, R. D. J. Med. Chem. 1993, 36, 1090-1099.
doi:10.1021/jm00060a017
PMid:8478906

[3]. Jones, D. H.; Slack, R.; Squires, S.; Wooldridge, K. R. H. J. Med. Chem. 1965, 8, 676-680.
doi:10.1021/jm00329a026

[4]. Sughen, J. K.; Yoloye, T. Pharm. Acta Helv. 1978, 58, 64-68.

[5]. Shams, El-Dine Sh A.; Hazzaa, A. A. B. Pharmazie, 1974, 29, 761-768.
PMid:4460001

[6]. Misato, T.; Ko, K.; Honma, Y.; Konno, K.; Taniyama, E. JP 77-25028 (A01N9/12), Chem. Abstr. 1977, 87, 147054a

[7]. Cansız, A.; Servi, S.; Koparır, M.; Altıntas, M.; Dığrak, M. J. Chem. Soc. Pak. 2001, 23, 237-239.

[8]. Stillings, M. R. Welbourn, A. P.; Walter, D. S. J. Med. Chem. 1986, 29, 2280-2284.
doi:10.1021/jm00161a025
PMid:3783590

[9]. Kane, J. M.; Dudley, M. W.; Sorensen, S. M.; Miller, F. P. J. Med. Chem. 1988, 31, 1253-1258.
doi:10.1021/jm00401a031
PMid:3373495

[10]. Chaha, V. K.; Ranwa, N. S.; Dadheech, P. K. J. Phytol. Res. 1998, 11, 201-202.

[11]. Sakata, M.; Shirakawa, Y.; Kamata, N.; Hiroshino, Y. S.; Jie, O. Y. J. Heterocyclic. Chem. 2000, 37, 269-271.
doi:10.1002/jhet.5570370208

[12]. Nadkarni, B. A.; Kamat, V. R.; Khadse, B. G. Arzneim. Force 2001, 51, 569-573.

[13]. Holla, B. S.; Akberali, P. M.; Shivananda, M. K. Farmaco 2001, 56, 919-927.
doi:10.1016/S0014-827X(01)01124-7

[14]. Hui, X. P.; Zhang, Y.; Xu, P. F.; Wang, Q.; Zhang, Q.; Zhang, Z. Y. Chin. J. Org. Chem. 2005, 25, 700-704.

[15]. B. S.; Rao, B. S.; Sarojini, B. K.; Akberali, P. M.; Kumari, N. S.; Eur. J. Med. Chem. 2006, 41, 657-663.
PMid:16616396

[16]. Zhou, S. N.; Zhang, L. X.; Jin, J. Y.; Zhang, A. J.; Lei, X. X.; He, J. S.; Lin J. W.; Zhang H, L. Phosphorus Sulfur and Silicon, 2007, 182, 419-432.
doi:10.1080/10426500600976884

[17]. Mobinikhaledi, A.; Foroughifar, N.; Goli, R. Phosphorus Sulfur and Silicon, 2005, 180, 2549- 2554.
doi:10.1080/104265090930191

[18]. Mobinikhaledi, A.; Foroughifar, N.; Mohammadlu, P.; Kalhor, M. S. Afr. J. Chem. 2008, 61, 141-143.

[19]. Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, Synthesis 2009, 15, 2557-2560.
doi:10.1055/s-0029-1217398

[20]. Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, S.; Moghanian, H.; Bodaghi Fard, M. A.; Kalhor, M. Tetrahedron Lett. 2009, 50, 836-839.
doi:10.1016/j.tetlet.2008.12.014

[21]. Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, S.; Bodaghi Fard, M. A.; Moghanian, M. J. Chin. Chem. Soc. 2009, 56, 1043-1047.

[22]. Galic, N.; Peric, B.; Kojic-Prodic, B.; Cimerman, Z. J. Mol. Stuc. 2001, 559, 187-194.
doi:10.1016/S0022-2860(00)00703-1

[23]. Wyrzykiewicz, E.; Prukah, D. J. Hetrocyclic. Chem. 1998, 35, 381-387.
doi:10.1002/jhet.5570350221

[24]. Palla, G.; Predieri, G.; Domiano, P. Tetrahedron 1986, 42, 3649-3654.
doi:10.1016/S0040-4020(01)87332-4

How to cite


Mobinikhaledi, A.; Foroughifar, N.; Khanpour, M.; Ebrahimi, S. Eur. J. Chem. 2010, 1(1), 33-36. doi:10.5155/eurjchem.1.1.33-36.5
Mobinikhaledi, A.; Foroughifar, N.; Khanpour, M.; Ebrahimi, S. Synthesis of some novel Schiff bases containing 1,2,4-triazole ring. Eur. J. Chem. 2010, 1(1), 33-36. doi:10.5155/eurjchem.1.1.33-36.5
Mobinikhaledi, A., Foroughifar, N., Khanpour, M., & Ebrahimi, S. (2010). Synthesis of some novel Schiff bases containing 1,2,4-triazole ring. European Journal of Chemistry, 1(1), 33-36. doi:10.5155/eurjchem.1.1.33-36.5
Mobinikhaledi, Akbar, Naser Foroughifar, Mansooreh Khanpour, & Sattar Ebrahimi. "Synthesis of some novel Schiff bases containing 1,2,4-triazole ring." European Journal of Chemistry [Online], 1.1 (2010): 33-36. Web. 11 Aug. 2020
Mobinikhaledi, Akbar, Foroughifar, Naser, Khanpour, Mansooreh, AND Ebrahimi, Sattar. "Synthesis of some novel Schiff bases containing 1,2,4-triazole ring" European Journal of Chemistry [Online], Volume 1 Number 1 (31 March 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.1.1.33-36.5

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2010, 1(1), 33-36 | doi: https://doi.org/10.5155/eurjchem.1.1.33-36.5 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  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 2010-2020 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.

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