Green and efficient protocol for synthesis a new series of fused pyrimidine derivatives incorporating thioamide moiety

https://doi.org/10.53730/ijhs.v6nS9.13136

Authors

  • Muna S. Abdullah University of Mosul, College of Girl Education, Department of Chemistry
  • Shaymaa. K. Younis Universityof Mosul, College of Science, Department of Chemistry

Keywords:

one-pot multicomponent, macrowave irradiation, thioamide, fused pyrimidines

Abstract

In the recent decades, heterocyclic compounds six membered ring occupied a great deals of attention due to its wide and varied applications in medical, pharmaceutical, agricultural and industrial fields. Herein in this work fused pyrimidine as active type of the mentioning above  have been successfully prepared  by using supreme green chemistry techniques represented by solid phase one-pot muticomponent reaction (Biginille reaction) and microwave irradiation via mixing equimolar of thioamide (phenyl thiourea)-dimedone and substituted Benzaldehyde in presence of (2% mole) of boric acid and few drops of glacial acetic acid as selective acid catalyst at power (700 watt) for (1 min) to afford 7,7, dimethyl-1-phenyl-4-aryl-3,4,6,7,8–5H-quinazolin-2-thione-5-one (1-7) as pure products with  high persentage.

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References

Benjamin H. Rotstein, Serge Zaretsky, Vishal Rai, and anderi K. Yudin .(2014) Small Heterocycles In Multicomponent Reactions Chem Rev 114,8323-8358

Cedric S. Graebin1,* , Felipe V. Ribeiro1 , Kamilla R. Rogerio2 and Arthur E. Kummerle1,* .(2019) Multicomponent reaction for the synthesis bioactive compounds :A review Current Organic Synthesis 16,855-899

Filho , A.,W.N., Ricardo; Brauer, C.N.Martin; A.T.Palm-Forster,Mieder ; N. Deolireiroc, Ronaldo;Wessjohann.A.,Luger (2012). Patented catalysts for the synthesis and biological applications of dihydropyrimidinones: reacent advances of the biginelli reaction,Source: Recent Patentson Catalysis, Vol.,No. 1,pp. 51-73 (23).

Ghasemzadeh M. A. Eshkevari B.M. Tavakoli .M and Zamani F. (2020) Metal-organic frameworks :advanced tools for multicomponent reaction . Green Chem.22,7265,7300

Jiang B. , Rajale T. , Wever W. , Tu S. , and Li G. (2010) Multicomponent Reaction for the Synthesis of Helerocycles Chem Asian 5,2318-2335

Kanevskaya, I. V., Bondartsova, A. S. Fedotova, O. V. (2020). Biginelli synthesis of regioisomeric 5, 6-dihydro-4H-benzo [4, 5] imidazo [1, 2-a] pyranopyrimidin-4-ones. Russian Journal of Organic Chemistry, 56, 1753-1757.

Liu, C., Huang, W., Zhang, J., Rao, Z., Gu, Y. and Jerome, F. (2021). Formal dehyde in multicomponent reactions. Green Chem., 23, 1447-1465.

Mohammed S.M.Moustafa A.H.,Ahmed ,N.EL-Syed,H.A.,Mohamed A.S.A.(2022),Nano-K2CO3-Catalyzed Biginelli-Type reaction: Regioselective synthesis, DFT study and Antimicrobial Activity of 4-aryl-6-methyl-5-phenyl-3,4-dihydropyrimidine-2(1H)-thiones. Russian Journal of Organic Chemistry , Vol.58, No.1,pp.136-143.

Mohanta., P. P., Pati, H. N. and Behera, A. K. (2020). The construction of flourophoric thiazolo- [2,3-b] quinazolinone derivatives: a multicomponent domino synthetic approach. Royal Society of Chemistry, 10, 15354-15359.

Nishimura, Y., Kikuchy, H., Kubo, T., Arai, R., Toguchi., Y, Boyuan sunaga, K, S, cho, H. (2022) synthesis of 4, 4-disubstituted 3, 4 dihydro pyrimidin-2(1h)-ones and thiones, the corresponding products of biginelli reaction using ketone, and their anti proliferative effect on hl-60cells. Chem-Pharma, 70,111-119.

Pääkkonen .I , Jääskeläiene .S , Kosheroy .I , O , Hirva .P . (2022) The effect of halogens in the coordination of 2-pyridinethioamide to gold centers .Polyhedron volume 226,116114 .

Patel, U., Parmar, B. Patel, P., Dadhania, A. and Suresh. E. (2021). The synthesis and characterization of Zn (II)/ cd (II) based MOFS by amixed ligand strategy: AZn (II) mof as a dual functional material for reversible dye adsorption and as a heterogeneous catalyst for the biginelli reaction. (Research Article) mater. Chem. Front ,5, 304-314.

Rogerio, K. R.,Graebin. C. S, et al .(2018). Synthesis and molecular modeling studies of pyrimidinones and pyrrolo [3, 4,-d]- pyrimidinodiones as new antiplasmodial compounds original article. Mem. Inst. Oswaldo cruz 113(8).

Sanli, Y., Tan, Zhao., Y, Wei., Y, Wong., D, Chen., R, and Tao., L. (2020). Anti-cancer polymers via the biginelli reaction. Journal ACsMacro Letters Manuseript ID mz 004963. R1.

Shaymaa K., Younis and Maysa'a, K. Shaker. (2017). Synthesis of some new fused pyrimidine compounds. Raf. J. Sci., Vol. 26, No. 1, pp. 92-99.

Suresh, S, T. (2012). Past present and future of the biginelli reaction: a critical perspective. Journal of Organic Chemistry, p 66-133.

Tahmasbi, M., Koukabi, N. and Armand pour, O. (2022). Sono and nano: A perfect synergy foreco compatible biginelli reaction heterocyclic, Communications ,Vol. 28,1.

Venkatesh, T., Bodke, Y. D., Manjunatha, B. and Kumar S. R. (2021). Synthesis, antitubercular activity and molecular docking study of substituted [1, 3] dioxino [4, 5-d] pyrimidine derivatives via facile CAN catalyzed biginelli reaction .Journal of Medicinal Chemistry ,Vol. 40, pages 1037-1049.

Zarenzhad, E.M Farjam, M., Iraqi, A. (2021). Synthesis and biological activity of pyrimidines-containing hybrids : Focusing on pharmacological application . Journal of Molecular Structure, Vol. 1230, 129833.

Published

30-09-2022

How to Cite

Abdullah, M. S., & Younis, S. K. (2022). Green and efficient protocol for synthesis a new series of fused pyrimidine derivatives incorporating thioamide moiety. International Journal of Health Sciences, 6(S9), 2844–2851. https://doi.org/10.53730/ijhs.v6nS9.13136

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Section

Peer Review Articles