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






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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.

4_2_180_184

Keywords


Chitosan; Hydrazonoyl halides; Ultrasound irradiation; Active chloromethylene; Benzopyranopyrimidine; Chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine

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DOI: 10.5155/eurjchem.4.2.180-184.767

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[1]. Sobhi M. Gomha, Kamal M. Dawood
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[2]. Sobhi M. Gomha, Mohamed G. Badrey, Mohamed M. Abdalla, Reem K. Arafa
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[3]. 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
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[4]. Abdou Abdelhamid, Sobhi Gomha, Nadia Abdelriheem, Saher Kandeel
Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents
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[5]. 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
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[6]. Abdou O. Abdelhamid, Sobhi M. Gomha, Ahmad S. Shawali
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HETEROCYCLES  91(11), 2126, 2015
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[7]. 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
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[8]. 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
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[9]. Sedigheh Akrami, Bahador Karami, Mahnaz Farahi
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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


Gomha, S.; Badrey, M. Eur. J. Chem. 2013, 4(2), 180-184. doi:10.5155/eurjchem.4.2.180-184.767
Gomha, S.; Badrey, M. Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives. Eur. J. Chem. 2013, 4(2), 180-184. doi:10.5155/eurjchem.4.2.180-184.767
Gomha, S., & Badrey, M. (2013). Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives. European Journal of Chemistry, 4(2), 180-184. doi:10.5155/eurjchem.4.2.180-184.767
Gomha, Sobhi, & Mohamed Gomaa Badrey. "Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives." European Journal of Chemistry [Online], 4.2 (2013): 180-184. Web. 30 Oct. 2020
Gomha, Sobhi, AND Badrey, Mohamed. "Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives" European Journal of Chemistry [Online], Volume 4 Number 2 (30 June 2013)

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DOI Link: https://doi.org/10.5155/eurjchem.4.2.180-184.767

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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

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