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

Samia Mohamed Sayed; Mohamed Ali Khalil; Mohamed Abd-Elmonem Raslan

doi:10.5155/eurjchem.5.2.356-362.1022

PDF

Published: Jun 30, 2014

DOI: https://doi.org/10.5155/eurjchem.5.2.356-362.1022

Keywords:

Thiophene, 1, 3-Thiazole, 3-Dithiolane, S, S-Dithioacetal, 3-Oxopropanenitrile, Thiazolo[2, 3-c]-1, 2, 4-triazole

Section

Research Article

Issue

Vol. 5 No. 2 (2014): June 2014

Dates

Received 2014-01-25
Accepted 2014-03-04
Published 2014-06-30

Samia Mohamed Sayed

Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt

Mohamed Ali Khalil

Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt

Mohamed Abd-Elmonem Raslan

Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt

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.

This Abstract was viewed 2346 times |

Article PDF downloaded 1074 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.

Links for Article

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)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2025 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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics