European Journal of Chemistry

Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety



Main Article Content

Samia Mohamed Sayed
Mohamed Ali Khalil
Mohamed Abd-Elmonem Raslan

Abstract

Coupling of 5-acetyl-2-amino-4-methylthaizole diazonium sulphate (1) with 3-chloro-pentane-2,4-dione (2) afforded the thiazolo[2,3-c]-1,2,4-triazole derivative, (5). Bormination of compound (5) followed by reaction with potassium cyanide afforded bis-3-oxo-propanenitrile derivative (7) which, reacts with CS2/NaH/CH3I to afford the ketene S,S-dithioacetal, (8). Synthesis of 1,3-dithiolane (11) and thiophene (15) derivatives have been reported.


icon graph This Abstract was viewed 2200 times | icon graph Article PDF downloaded 991 times

How to Cite
(1)
Sayed, S. M.; Khalil, M. A.; Raslan, M. A.-E. Synthesis of Pyrazole, 1,3-Dithiolan and Thiophene Derivatives Pendant to thiazolo[2,3-C]-1,2,4-Triazole Moiety. Eur. J. Chem. 2014, 5, 356-362.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Pattan, S. R.; Reddy, K. V. V.; Manvi, F. V.; Desai, B. G.; Bhat, A. R. Indian J. Chem. 2006, 45B, 1778-1781.

[2]. Pattan, S. R.; Shamrez, A. M.; Pattan, J. S.; Purohit, S. S.; Reddy, K. V. V.; Nataraj, B. R. Indian J. Chem. 2006, 45B, 1929-1932.

[3]. Narayana, B.; Raj, K. K. V.; Ashalatha, B. V.; Kumari, N. S. Indian J. Chem. 2006, 45B, 1704-1709.

[4]. Altintas, H.; Ates, O.; Kocabalkanli, A.; Birteksoz, S.; Otuk, G. Indian J. Chem. 2005, 44B, 585-509.

[5]. Kane, J. M.; Baron, B. M.; Dudley, B. M.; Sorensen, S. M.; Staeger, M. A.; Miller, F. P. J. Med. Chem. 1990, 33, 2772-2777.
http://dx.doi.org/10.1021/jm00172a015

[6]. Kucukguzel, I.; Kucukguzel, S. G.; Rollas, S.; Otuk-Sanis, G.; Ozdemir, O.; Bayrak, I.; Altug, T.; Stables, J. P. II Farmaco 2004, 59, 893-901.
http://dx.doi.org/10.1016/j.farmac.2004.07.005

[7]. Modi, V. P.; Jani, D. H.; Patel, H. S. Orbital Elec. J. Chem. Campo Grand. 2011, 3, 68-79.

[8]. Rollas, S.; Kalyoncuoghu, N.; Sur-Altiner, D.; Yegenouglu, Y. Pharmazie 1993, 48, 308-309.

[9]. Chollet, J. F.; Bonnemain, J. L.; Miginiac, L.; Rohr, O. J. Pestic. Sci. 1990, 29, 427-435.
http://dx.doi.org/10.1002/ps.2780290407

[10]. Murabayashi, A.; Masuko, M.; Niikawa, M.; Shirane, N.; Futura, T.; Hayashi, Y.; Makisumi, Y. J. Pestic. Sci. 1991, 16, 419-427.
http://dx.doi.org/10.1584/jpestics.16.419

[11]. Gilbert, B. E.; Knight, V. Antimicrob. Agents Chemother. 1986, 30, 201-205.
http://dx.doi.org/10.1128/AAC.30.2.201

[12]. Holla, B. S.; Veerendra, B.; Shivanada, M. K.; Poojary, B. Eur. J. Med. Chem. 2003, 38, 759-767.
http://dx.doi.org/10.1016/S0223-5234(03)00128-4

[13]. Turan-Zitoumi, G.; Sivaci, M. F.; Kilic, S.; Erol, K. Eur. J. Med. Chem. 2001, 36, 685-689.
http://dx.doi.org/10.1016/S0223-5234(01)01252-1

[14]. Bekircan, O.; Kucuk, M.; Kahveci, B.; Kolayli, S. Arch. Pharm. 2005, 338, 365-372.
http://dx.doi.org/10.1002/ardp.200400964

[15]. Wade, P. C.; Vogt, B. R.; Kissick, T. P.; Simpkins, L. M.; Palmer, D. M.; Millonig, R. C. J. Med. Chem. 1982, 25, 331-333.
http://dx.doi.org/10.1021/jm00345a021

[16]. Gruta, A. R.; Bhargava, K. P. Pharmazie 1978, 33, 430-434.

[17]. Modzelewska, B.; Kalabun, J. Pharmazie 1999, 54, 503-505.

[18]. Malbec, F.; Milcent, R.; Vicart, P.; Bure, A. M. J. Heterocycl. Chem. 1984, 21, 1769.
http://dx.doi.org/10.1002/jhet.5570210641

[19]. Milcent, R.; Vicart, P.; Bure, A. M. Eur. J. Med. Chem. 1983, 18, 215-217.

[20]. Gulerman, N.; Rollas, S.; Kiraz, M.; Ekinci, A. C.; Vidin, A. II Farmaco 1997, 52, 691-695.

[21]. Ikizler, A. A.; Johansson, C. B.; Bekircan, O.; Celik, C. Acta Polon. Pharm-Drug Res. 1999, 56, 283-288.

[22]. Shujuan, S.; Hongxiang, L.; Gao, Y.; Fan, P.; Ma, B.; Ge, W.; Wang, X. J. Pharm. Miomed. Anal. 2004, 34, 1117-1124.
http://dx.doi.org/10.1016/j.jpba.2003.11.013

[23]. Clemon, M.; Coleman, R. E.; Verma, S. Cancer Treat. Rev. 2004, 30, 325-332.
http://dx.doi.org/10.1016/j.ctrv.2004.03.004

[24]. Johnston, G. A. R. Curr. Top. Med. Chem. 2002, 2, 903-913.
http://dx.doi.org/10.2174/1568026023393453

[25]. Sauzem, P. D.; Machado, P.; Rubin, M.; Das, S. G.; Faber, H. B.; Souza, A. H.; Mello, C. F.; Beck, P.; Burrow, R. A.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. Eur. J. Med. Chem. 2008, 43, 1237-1247.
http://dx.doi.org/10.1016/j.ejmech.2007.07.018

[26]. Abu-Melha, S. Archiv der Pharmazie 2013, 346, 912-921.
http://dx.doi.org/10.1002/ardp.201300195

[27]. Chakrabarti, J. K.; Horsman, L.; Hotten, T. M.; Pullar, I. A.; Tupper, D. E.; Wright, F. C. J. Med. Chem. 1980, 23, 878-884.
http://dx.doi.org/10.1021/jm00182a013

[28]. Ram, V. J.; Pandey, H. K.; Vlientick, A. J. J. Heterocycl. Chem. 1981, 18, 1277-1280.
http://dx.doi.org/10.1002/jhet.5570180111

[29]. Mabkhot, Y. N.; Kheder, N. A.; Al-Majid, A. M. Molecules 2010, 15, 9418-9426.
http://dx.doi.org/10.3390/molecules15129418

[30]. Sayed, S. M.; Selim, M. A.; Raslan, M. A.; Khalil, M. A. Heteroatom Chem. 2000, 11, 362-369.
http://dx.doi.org/10.1002/1098-1071(2000)11:5<362::AID-HC7>3.0.CO;2-N

[31]. Raslan, M. A. J. Chin. Chem. Soc. 2000, 47, 961-965.

[32]. Raslan, M. A.; Khalil, M. A. Heteroatom Chem. 2003, 14, 114-120.
http://dx.doi.org/10.1002/hc.10109

[33]. Raslan, M. A.; Sayed, S. M. J. Chin. Chem. Soc. 2003, 50, 909-916.

[34]. Sayed, S. M.; Khalil, M. A.; Ahmed, M. A.; Raslan, M. A. Synth. Comm. 2002, 32, 481-495.
http://dx.doi.org/10.1081/SCC-120002134

[35]. Sayed, S. M.; Raslan, M. A.; Khali, M. A.; Dawood, K. M. Heteroatom Chem. 1999, 10, 385-390.
http://dx.doi.org/10.1002/(SICI)1098-1071(1999)10:5<385::AID-HC8>3.0.CO;2-O

[36]. Maradiya, H. R.; Patel, V. S. J. Braz. Chem. 2001, 12. 710-714.

[37]. Ibrahim, M. K. A.; Elghandour, A. H.; Abou-hadeed, K. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 60, 119-123.
http://dx.doi.org/10.1080/10426509108233932

[38]. Potts, K. T.; Husain, S. J. Org. Chem. 1971, 36, 10-13.
http://dx.doi.org/10.1021/jo00800a004

[39]. Fadda, A. A.; Mukhtar, M. M.; Refat, H. M. American J. Org. Chem. 2012, 2, 32-42.

Supporting Agencies

Aswan Faculty of Science, Aswan University, Egypt
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).