European Journal of Chemistry 2013, 4(2), 180-184 | doi: | Get rights and content


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


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.



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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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. 21 Feb. 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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