Selective approaches to synthesize a new series of fused 4-amino pyrimidine derivatives by using of 4- amino nicotino nitrile as an effective precursor
Keywords:
Fused pyrimidine, Green chemistry, One-pot multicomponent reaction, 4-amino nicotino nitrile, Microwave irradiationAbstract
Pyrimidines and it's derivatives are one of the most fascinating type of six membered heterocyclic compounds which received a great deals of attention due to it`s diverse importance and activity in many different field such as biological, medicinal, pharmaceutical and also in industrial and agricultural field. In this presentation, fused 4-amino pyrimidine derivatives were achieved using green chemistry technique represented by solid phase one–pot multicomponent reaction, microwave irradiation and grinding and also by traditional methods. Firstly, equimolar of aromatic(heterolytic) amines, piperonal and malononitriles were grinding for few minutes then accelerated by microwave irradiation (MWI) at (270 watt) for 3 minutes to afford fused 4-amino nicotino nitrile (1a-e) which then underwent cycloaddition reaction with formamide, urea and thiourea via traditional methods using acidic or basic conditions to afford a new series of fused 4-amino pyrimidines represented by compounds (2a-e), (3a-e) and (4a-e) respectively. All prepared compounds were illustrated by the available physical and spectral methods.
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Amer, A., El-Eraky, W. I., & Mahgoub, S. (2018). Synthesis, characterization and antimicrobial activity of some novel quinoline derivatives bearing pyrazole and pyridine moieties. Egyptian Journal of Chemistry, 61(Conference issue (14th Ibn Sina Arab Conference on Heterocyclic Chemistry and its Applications (ISACHC 2018), 30 March-2 April 2018, Hurgada, Egypt).), 1-8.
Aslam, N., White, J., Zafar, A. M., Jabeen, M., Ghafoor, A., Sajjid, N., . . . Khan, M. A. (2018). 4H-Pyrano [2, 3-c] pyrazoles: a review.
Bariwal, J. B., Trivedi, J. C., & Eycken, E. V. (2010). Microwave irradiation and multicomponent reactions. Synthesis of Heterocycles via Multicomponent Reactions II, 169-230.
Boger, D. L., Ishizaki, T., Wysocki Jr, R. J., Munk, S. A., Kitos, P. A., & Suntornwat, O. (1989). Total synthesis and evaluation of (.+-.)-N-(tert-butoxycarbonyl)-CBI,(.+-.)-CBI-CDPI1, and (.+-.)-CBI-CDPI2: CC-1065 functional agents incorporating the equivalent 1, 2, 9, 9a-tetrahydrocyclopropa [1, 2-c] benz [1, 2-e] indol-4-one (CBI) left-hand subunit. Journal of the American Chemical Society, 111(16), 6461-6463.
Borah, B., Dwivedi, K. D., & Chowhan, L. R. (2021). Applications of pyrazolone in multicomponent reactions for the synthesis of dihydropyrano [2, 3-c] pyrazoles and spiro-pyrano [2, 3-c] pyrazoles in aqueous medium. ARKIVOC: Online Journal of Organic Chemistry, 2021.
Darwish, E. S., Abdelrahman, M. A., & Salaheldin, A. M. (2011). Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines. Zeitschrift für Naturforschung B, 66(6), 597-602.
El-Gazzar, A., Hegab, M., Swelam, S., & Aly, A. (2002). Studies with polyfunctionality substituted heterocycles: Novel syntheses of thienopyrimido-1, 2, 4-triazoles. Phosphorus, Sulfur, and Silicon and the Related Elements, 177(1), 123-136.
Farghaly, A. M., AboulWafa, O. M., Elshaier, Y. A., Badawi, W. A., Haridy, H. H., & Mubarak, H. A. (2019). Design, synthesis, and antihypertensive activity of new pyrimidine derivatives endowing new pharmacophores. Medicinal Chemistry Research, 28(3), 360-379.
Farouk Elsadek, M., Mohamed Ahmed, B., & Fawzi Farahat, M. (2021). An overview on synthetic 2-aminothiazole-based compounds associated with four biological activities. Molecules, 26(5), 1449.
Fathalla, O., Zeid, I., Haiba, M., Soliman, A., Abd-Elmoez, S. I., & El-Serwy, W. (2009). Synthesis, antibacterial and anticancer evaluation of some pyrimidine derivatives. World J Chem, 4(2), 127-132.
Fawzy, N. M., Roaiah, H. M., Awad, E. M., Wietrzyk, J., Milczarek, M., & Soliman, A. M. (2018). Synthesis of new indole derivatives using one-pot multicomponent reaction with antiproliferative towards normal and cancer cell lines. Egyptian Pharmaceutical Journal, 17(2), 85.
Ghorab, M. M., Noaman, E., Ismail, M. M., Heiba, H. I., Ammar, Y. A., & Sayed, M. Y. (2006). Novel antitumor and radioprotective sulfonamides containing pyrrolo [2, 3-d] pyrimidines. Arzneimittelforschung, 56(06), 405-413.
Kumar, S., Deep, A., & Narasimhan, B. (2019). A review on synthesis, anticancer and antiviral potentials of pyrimidine derivatives. Current Bioactive Compounds, 15(3), 289-303.
Maddila, S., Gorle, S., Seshadri, N., Lavanya, P., & Jonnalagadda, S. B. (2016). Synthesis, antibacterial and antifungal activity of novel benzothiazole pyrimidine derivatives. Arabian Journal of Chemistry, 9(5), 681-687.
Mahfoudh, M., Abderrahim, R., Leclerc, E., & Campagne, J. M. (2017). Recent approaches to the synthesis of pyrimidine derivatives. European Journal of Organic Chemistry, 2017(20), 2856-2865.
Mallikarjunaswamy, C., Mallesha, L., Bhadregowda, D., & Pinto, O. (2017). Studies on synthesis of pyrimidine derivatives and their antimicrobial activity. Arabian Journal of Chemistry, 10, S484-S490.
Mohamed, M. S., Rashad, A. E., Zaki, M. E., & Fatahala, S. S. (2005). Synthesis and antimicrobial screening of some fused heterocyclic pyrroles. Acta Pharmaceutica, 55(3), 237-249.
Naik, T., & Chikhalia, K. (2007). Studies on synthesis of pyrimidine derivatives and their pharmacological evaluation. E-Journal of Chemistry, 4(1), 60-66.
Orlov, P. V. (2018). Application of derivatives of pyrazolotriazinones to improve the vegetative growth of barley. paper presented at the chemistry of nitrogen containing heterocycles, Kharkiv, Ukraine.
Prachayasittikul, S., Pingaew, R., Worachartcheewan, A., Sinthupoom, N., Prachayasittikul, V., Ruchirawat, S., & Prachayasittikul, V. (2017). Roles of pyridine and pyrimidine derivatives as privileged scaffolds in anticancer agents. Mini Reviews in Medicinal Chemistry, 17(10), 869-901.
Raghavendra, M., Bhojya Naik, H. S., & Sherigara, B. S. (2006). Microwave induced synthesis of thieno [2, 3-b] quinoline-2-carboxylic acids and alkyl esters and their antibacterial activity. Journal of Sulfur Chemistry, 27(4), 347-351.
Shi, F., Tu, S., Fang, F., & Li, T. (2005). One-pot synthesis of 2-amino-3-cyanopyridine derivatives under microwave irradiation without solvent. Arkivoc, 2005(1), 137-142.
Thakur, V. (2011). Synthesis of enamines and their bromination.
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