Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives
Sobhi Mohamed Gomha (1,*)
, Mohamed Gomaa Badrey (2) (1) Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
(2) Chemistry Department, Faculty of Science, Fayoum University, El-Fayoum, 63514, Egypt
(*) Corresponding Author
Received: 09 Mar 2013 | Revised: 26 Mar 2013 | Accepted: 12 Apr 2013 | Published: 30 Jun 2013 | Issue Date: June 2013
Abstract
The reaction between 2-mercapto-3H-chromeno[4,3-d]pyrimidine-4,5-dione (1) or its 2-methylthio derivative (7) with hydrazonoyl halides (2) in dioxane under ultrasound irradiation in the presence of chitosan yielded chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives (5a-r). On the other hand, the reaction of compound 1 with the appropriate active chloromethylene compounds (9b, h and m) followed by coupling the products with benzenediazonium chloride afforded the azo coupling products which converted in situ to compound 5. The reaction mechanism was proposed and the structure of the newly synthesized compounds were established on the basis of spectral data (Mass, IR, 1H and 13C NMR) and elemental analyses.
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
Full Text:
PDF
DOI: 10.5155/eurjchem.4.2.180-184.767
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 1822 times |
PDF Article downloaded 1384 times
Citations
[1]. Sobhi M. Gomha, Kamal M. Dawood
Synthetic Utility of Pyridinium Bromide: Synthesis and Antimicrobial Activity of Novel 2,4,6‐Trisubstituted Pyridines Having Pyrazole Moiety
Journal of Heterocyclic Chemistry 54(3), 1943, 2017
DOI: 10.1002/jhet.2790
[2]. Mohamed G. Badrey, Sobhi M. Gomha, Aboubakr H. Abdelmonsef, Ahmed A. M. El-Reedy
Syntheses and Molecular Docking Analysis of Some New Thiazole and Thiazine Derivatives as Three Armed Molecules with a Triazine Ring as a Core Component: A Search for anti-Obesity Agents
Polycyclic Aromatic Compounds , 1, 2023
DOI: 10.1080/10406638.2023.2173617
[3]. Sobhi M. Gomha, Mohamed G. Badrey, Mohamed M. Abdalla, Reem K. Arafa
Novel anti-HIV-1 NNRTIs based on a pyrazolo[4,3-d]isoxazole backbone scaffold: design, synthesis and insights into the molecular basis of action
Med. Chem. Commun. 5(11), 1685, 2014
DOI: 10.1039/C4MD00282B
[4]. Abdelwahed R. Sayed, Sobhi M. Gomha, Thoraya A. Farghaly
Synthesis and Characterization of Bisimidazoles, Bistriazoles, Bisthiadiazoles, and Bisthiazoles from Novel Bishydrazonoyl Dichlorides
Journal of Heterocyclic Chemistry 53(1), 255, 2016
DOI: 10.1002/jhet.2320
[5]. Abdou Abdelhamid, Sobhi Gomha, Nadia Abdelriheem, Saher Kandeel
Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents
Molecules 21(7), 929, 2016
DOI: 10.3390/molecules21070929
[6]. Abdou Abdelhamid, Ibrahim El Sayed, Mohamed Hussein, Mangoud Mangoud
Synthesis and Antimicrobial Activity of Some New Thiadiazoles, Thioamides, 5-Arylazothiazoles and Pyrimido[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines
Molecules 21(8), 1072, 2016
DOI: 10.3390/molecules21081072
[7]. Abdou O. Abdelhamid, Sobhi M. Gomha, Ahmad S. Shawali
Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, 1,3,4-Thiadiazole and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine Derivatives Incorporating Pyrazole Moiety
HETEROCYCLES 91(11), 2126, 2015
DOI: 10.3987/COM-15-13319
[8]. Ikhlass M. Abbas, Magda A. Abdallah, Sobhi M. Gomha, Mariam S. H. Kazem
Synthesis and Antimicrobial Activity of Novel Azolopyrimidines and Pyrido-Triazolo-Pyrimidinones Incorporating Pyrazole Moiety
Journal of Heterocyclic Chemistry 54(6), 3447, 2017
DOI: 10.1002/jhet.2968
[9]. Sobhi Gomha, Sayed Ahmed, Abdou Abdelhamid
Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles, and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole Moiety
Molecules 20(1), 1357, 2015
DOI: 10.3390/molecules20011357
[10]. Sedigheh Akrami, Bahador Karami, Mahnaz Farahi
A new and green approach for regiospecific synthesis of novel chromeno‐triazolopyrimidin using tungstic acid immobilized MCM‐41 as a reusable catalyst
Journal of Heterocyclic Chemistry 57(6), 2446, 2020
DOI: 10.1002/jhet.3960
[11]. Awad I. Said, Márta Palkó, Matti Haukka, Ferenc Fülöp
Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides: Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones
Molecules 25(23), 5673, 2020
DOI: 10.3390/molecules25235673
[12]. Namdeo T. Dhokale, Satish B. Kale, Sadashiv S. Nagre, Shankaraiah G. Konda, Navanath R. Dalvi
A convenient and efficient synthesis of 2-thio-5-hydroxy-5H-[1]benzopyrano[4,3-d] pyrimidines via ultrasonic irradiation compared with conventional method
Current Research in Green and Sustainable Chemistry 5, 100282, 2022
DOI: 10.1016/j.crgsc.2022.100282
References
[1]. Mitra, A. K.; De, A.; Karchaudhuri, W.; Misra, S. K.; Mukhopulhyay, A. K. J. Indian Chem. Soc. 1998, 75, 666-671.
[2]. Romines, K. R.; Morris, J. K.; Howe, W. J.; Tomich, P. K.; Horng, M. M.; Chong, K. T.; Hin Shaw, R. R.; Anderson, D. J.; Strohbach, T. W.; Tumer, S. R.; Mizsak, S. A. J. Med. Chem. 1996, 39, 4125-4130.
http://dx.doi.org/10.1021/jm960296c
PMid:8831779
[3]. Yev, J.; Laurent, B.; Herve, G.; Bernard, R.; Gerard, L. A.; Edwige, D.; Alain, X. Eur. J. Med. Chem. 2001, 36, 127-136.
http://dx.doi.org/10.1016/S0223-5234(00)01207-1
[4]. Unangst, P. C.; Capiris, T.; Heffner, D. T. C.; Mackenzie, R. G.; Miller, S. R.; Pugsley, T. A. ; Wise, L. D. J. Med. Chem. 1997, 40, 2688-2693.
http://dx.doi.org/10.1021/jm970170v
PMid:9276014
[5]. Singh, J.; Kaur, J.; Nayyar, S.; Bhandari, M.; Kad, G. L. Indian J. Chem. 2001, 40B, 386-390.
[6]. Yadav, S. J.; Reddy, B. V. S.; Reddy, K. B.; Raj, K. R.; Prasad, A. R. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
[7]. Xu, H.; Liao, W. M.; Li, H. F. Ultrason. Sonochem. 2007, 14, 779-782.
http://dx.doi.org/10.1016/j.ultsonch.2007.01.002
PMid:17350316
[8]. Gomha, S. M.; Khalil, Kh. D. Molecules 2012, 17, 9335-9347.
http://dx.doi.org/10.3390/molecules17089335
PMid:22864241
[9]. Farghaly, T. A.; Abbas, I.; Abdalla, M. M. M.; Mahgoub, R. O. Arkivoc 2012, 6, 57-70.
http://dx.doi.org/10.3998/ark.5550190.0013.606
[10]. Gomha, S. M.; Riyadh, S. M. Arkivoc 2009, 11, 58-68.
[11]. Hassaneen, H. M.; Hassaneen, H. M. E.; Mohammed, Y. Sh. Nat. Sci. 2011, 3, 651-660.
[12]. El-Deen, I. M.; Ibrahim, H. K. Phosphorous, Sulfur, Silicon 2000, 160, 241-250.
[13]. Mohammed, F. K.; Essawy, A. I.; Badrey, M. G. Asian J. Chem. 2009, 21, 5873-5887.
[14]. Shawali, A. S.; Abdelhamid, A.O. Bull. Chem. Soc. Jpn. 1976, 49, 321-324.
http://dx.doi.org/10.1246/bcsj.49.321
[15]. Bullow, C.; King, E. Liebigs Ann. 1924, 439, 211-220.
http://dx.doi.org/10.1002/jlac.19244390114
[16]. Dieckmann, W.; Platz, O. Ber. Dtsch. Chem. Ges. 1906, 38, 2989-2995.
[17]. Curtius, T. J. Prakt. Chem. 1899, 51, 168-169.
[18]. Gomha, S. M. Monatsh. Chem. 2009, 140, 213-220.
http://dx.doi.org/10.1007/s00706-008-0060-z
[19]. Jung, J. C.; Watkins, E. B. Heterocycles 2005, 65, 77-94.
http://dx.doi.org/10.3987/COM-04-10216
[20]. Bedford, G. R.; Tylor, P. J.; Webb, G. A. Mag. Res. Chem. 1995, 33, 389-394.
http://dx.doi.org/10.1002/mrc.1260330511
[21]. Reiter, J.; Bongo, L.; Dyortsok, P. Tetrahedron 1987, 43, 2497-2504.
http://dx.doi.org/10.1016/S0040-4020(01)81656-2
[22]. Abdelhamid, A. O.; Fahmi, A. A.; Ali, A. B. Eur. J. Chem. 2011, 2(4), 544‐551.
http://dx.doi.org/10.5155/eurjchem.2.4.544-551.478
[23]. Hassan, N. A. J. Sulfur Chem. 2006, 27, 595-603.
http://dx.doi.org/10.1080/17415990600954841
[24]. Khodair, A. J. Heterocycl. Chem. 2002, 39, 1153-1160.
http://dx.doi.org/10.1002/jhet.5570390607
[25]. Abdel‐Aziem, A.; El‐Gendy, M.S.; Abdelhamid, A. O. Eur. J. Chem. 2012, 3(4), 455‐460.
http://dx.doi.org/10.5155/eurjchem.3.4.455-460.683
[26]. Abarca, B.; Jimenez, M.; Jones, G.; Soriano, C. J. Chem. Res. (M) 1986, 3358-3367.
[27]. Elliott, A. J.; Callaghan, P. D.; Gibson, M. S.; Nemeth, S. T. Can. J. Chem. 1975, 53, 1484-1490.
http://dx.doi.org/10.1139/v75-206
[28]. Elliott, A. J.; Gibson, M. S.; Kayser, M. M.; Pawelchack, G. A. Can. J. Chem. 1973, 51, 4115-4120.
http://dx.doi.org/10.1139/v73-615
How to cite
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.4.2.180-184.767
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2013, 4(2), 180-184 | doi: https://doi.org/10.5155/eurjchem.4.2.180-184.767 | 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.