Green chemistry as efficient approache to achieve a new series of heterocyclic compounds

https://doi.org/10.53730/ijhs.v6nS8.13124

Authors

  • Falknaz R. Kadier University of Mosul, College of Education and pure Science, Department of Chemistry,Mosul, Iraq
  • Shaymaa K. Younis University of Mosul, College of Science, Department of Chemistry,Mosul,Iraq

Keywords:

green chemistry, one-pot multicomponent reaction, grinding technique, microwave irradiation, imidazole, 1,2,4 triazole

Abstract

Solid phase one-pot Multicomponent reaction was used widely to achieved  a board spectrum of heterocyclic compounds due to it’s supreme properties starting from four component mixture of piperonal binzil, p-phenylene diamine and ammonium acetate which was reacted directly through grinding then microwave irradiation at (270 watt) for (8 min) in a cidic media to afford 1-N(p-aminophenyl)-2-(piperonyl-5-yl)-5-hydroxy-4, 5-diphenyl-2H-imidazole (1) which then converted to its N'-aroyl derivatives (2-4) through it’s reaction with substituted benzoyl chloride in basic media terminated by direct reaction with acetic anhydride  to obtained N'-acetyl-N'-aroyl derivative (5-7) followed by inter cyclization reaction with hydrazine hydrate (99%) to achieve 1,2,4-trizole derivatives (8-10) in basic media. The assigned structure of the prepared compounds were corroborated by the available physical and spectral methods.

Downloads

Download data is not yet available.

References

Adeyemi, O. S., Eseola, A. O. Plass, W., Atolani, O., Sugi, T., Han, Y.,and Kayode, O. T. (2020). Imidazole derivatives as antiparasitic agents and use of molecular modeling to investigate the structure-activity relationship. Parasitology Research, 119(6): 1925-1941.

Altindag, F. D., Salglik, B. N., Cevik, U. A., Iskdag, I., Ozkay, Y., and Gencer, H. K. (2019). Novel imidazole derivatives as antifungal agents: Synthesis biological evaluation, ADME prediction and molecular docking studies. Phospours Sulfur, and Silicon and the Related Elements.

Barany,G. & Merrifield,R.B.,(1977).A new amino protecting group removable by reduction.Chemistry of the dithiasuccinoyl (DTs) function. Journal of the American Chemical Society,99(22):7363-7365.

Bhade MW.,Rajput PR.(2016),Design and Synthesis of some imidazole moiety as antibacterial agent.Int. J.Appl.Pure. Sci.Agric, 2(11):80-84.

Catalant, J. Faberio, F., Claramunt, R. M., Santa Maria , M. D., Foces-Foces, M. D. L. C., Hernandez Cano, F., ….and Sastre , R.(1992). New ultraviolet stabilizers: 3-and5-(2'-hydroxyphenyl) pyrazoles. Journal of the American Chemical Society, 114(13): 5039-5048.

Chandgude,A.(2017).Multicomponent reactions:development,scope, and applications.University of Groningen. PhD Thesis,Chapter 1.pp.7-28

Chopra, P. N., & Sahu, J. K. (2019). Biological Significance of Imidazole-based Analogues in New Drug Development. Current Drug Discovery Technologies.

Dong, H. R. Wu, J. G., and Huo, G. Y. (2022). Design, synthesis and biological studies of some new imidazole1-2,3-triazole hybrid derivatives. Journal of Molecular structure 1256, 132516.

Finer,I.L.,(1977)."Organic Chemistry".Longman,Vol.2,pp.17-18.

Fu, Q., Cai, P. P., Cheng, L. Zhong, L. K., Tan, C. X., Shen, Z. H.,…and Liu, X. H. (2020). Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor. Pest Management Science, 76(3): 868-879.

Gebre, S.H. (2021). Recent development in the fabrication of magnetic nanoparticles for the syntheses of trisubstituted pyridines and imidazole: A green approach. Synthetic communications, 51(11), :1669-1699.

Harmastuti,N., Herowati,R., Susilowati,D., Pranowo,H.D. and Mubarika, S.,(2012).Synthesis and cytotoxic activity of chalcone derivatives on human breast cancer cell lines. Indonesian Journal of Chemistry,12(3):261-267.

Hernàndez-V'azquez, E., Ocampo-Montalban, H., Ceron-Romero, L., Cruz, M., Gómez-Zamudio, J., Hiriart-Valencia, G.,….and Estrada-Soto, S.(2017). Antidiabetic, antidyslipidemic and toxicity profile of ENV-2: A potent pyrazole derivative againts diabetes and related diseases. European Journal of Pharmacology, 803: 159-166.

Hurd, C. D., and PRAPAS, A. G. (1959). Preparation of acyclic imides. The Journal of Organic Chemistry, 24(3): 388-392.

Johnson,R.D.,Lane,G.A.,Koulman,A.Cao,M.,Fraser,K.,Fleetwood,D.,J. and Johnson,L.J.,(2015).A novel family of cyclic oligopeptides derived from ribosomal peptide synthesis of an in planta-induced gene,gig A,in Epichloë endophytes of grasses.Fungal Genetics and Biology,85,14-24.

Kabaehnik,Martin I.;Medved,T.Ya.(1952). A new method for the synthesis of α-amino phosphoric acids. Doklady Akademii Nauk SSSR (in Russian),83:689ff.

Kamel, M. M. (2015). Conveninet synthesis, characterization, cytotocity and toxicity pyrazole derivatives. Asc. 62 (1):136-151.

Karrouchi, K., Radi, S., Ramli, Y., Taoufic, J., Mabkhot, Y. N., Al-Aizari, F. A., and Ansar, M. H. (2018). Synthises and pharmacological activities of pyrazole derivatives: A review Molecules, 23(1): 134.

Khan, M. F., Alam, M. M., Verma, G., Akhtar, W., Akhtar, M.,and Shaquiquzzaman, M. (2016). The therapeutic voyage of pyrazole and its analogs: a review. Eropean Journal of Medicinal Chemistry, 120: 170-201.

Kokalj, A., Kovačević, N., Peljhan, S., Finsgar, M., Lesar, A., and Milošev, I. (2011). Triazole, benzotriazole, and naphthotriazole as copper corrosion inhibitors: I. Molecular electronic and adsorption properties. Chem.Phys.Chem., 12 (8): 3547-3555.

Lee,J.,Hong,M.,Jung,Y.,Cho,E.J. and Rhee,H.(2012).Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides.Tetrahedron,68(8):2045-2051.

Maxut,A., Noziere,B.,Fenet, B.,& Mechakra, H.,(2015), Formation mechanisms and yields of small imidazoles from reactions of glyoxal with NH4+ in water at neutral Ph.Physical Chemistry Chemical Physics,17(31),20416-20424.

Mishra, A., Aslam, J., Verma, C., Quraishi, M.A., and Ebenso, E.E. (2020). Imidazoles as high effective heterocyclic corrosion inhibitors for metals and alloys in aqueous electrolytes: A review. Journal of Taiwan institute Chemical Engineers, 114: 341-358.

Mocelo-Castelle,R.,Villanueva-Novelo,C.,Caceres-Castillo,R.M., Quijano-Quinones,R.F.,Quesadas-Rojas,M. and Mena-Rejon,G.J. (2015). 2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents:Synthesis, Biological Evaluation and Qsar Studies

Moosavi-Zare, A. R., Asgari, Z., Zare, A., and Zolfigol, M. A. (2015). One pot multi-component synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles using sulfonic acid-functionalized pyridinium chloride as an efficient and recyclable catalyst. Scientia Iranica, 22(6): 2254-2261.

Nalage,S.V.,Kalyankar,M.B.,Patil,V.S.,Bhosale,S.V.,Deshmukh,S.U.,Pawar, R.P.(2010).An efficient noncatalytic protocol for the synthesis of trisubstituted imidazole in polyethylene glycol using microwaves.The open Catalysis Journal,3(1).

Narasimhan, B., Sharma, D. and Kumar, P.(2011). Biological importance of imidazole nucleus in the new millennium. Medicinal Chemistry Research, 20(8): 1119-1140.

Nascimento, M. V. P., Munhoz, A., Theindl, L. C., Mohr, E. T. B., Saleh, N., Parisotto, E.B. and Dalmarco, E.M. (2018). A novel tetrasubstituted imidazole as prototype for the development of anti-inflammatory drugs.Inflammation, 41(4): 1334-1348.

Patel H. M., Noolvi M. N., Kamboj,S. and Cameotra S. S.,(2016) “Synthesis and antimicrobial evaluation of novel 1,3, 4-thiadiazole derivatives of 2-(4-formyl-2-methoxyphenoxy) acetic acid,” Arabian Journal of Chemistry, 9:pp. S1283-S1289.

Ramachandran R., Rani M., Senthan S., Jeong Y.T. and Kabilan S.,(2011) “Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives,” European Journal of Medicinal Chemistry, Vol. 46, No. 5: pp. 1926-1934.

Shalini, K., Sharma, P.K. and Kumar, N. (2010). Imidazole and its biological activities: A review. Der Chemica Sinica, 1(3): 36-47.

Siwch, A. and Verma, P. K. (2021). Synthesis and therapeutic potential of imidazole containing compounds. BMC Chemistry, 15(1): 1-69.

Taslimi, P., Erden, Y., Mamedov, S. Zeynalova, L., Ladokhina, N., Tas, R. and Gulcin, I. (2021). The biological activities, molecular docking studies, and anticancer effects of 1-arylsuphonypyrazole derivatives. Journal of biomlecular structure and dynamics, 39(9): 3336-3345.

Verma ,A.,Joshi,S.,and Singh D.,(2013). Imidazole:having versatile biological activitive Journal of Chemistry,13:1-12.

Published

30-09-2022

How to Cite

Kadier, F. R., & Younis, S. K. (2022). Green chemistry as efficient approache to achieve a new series of heterocyclic compounds. International Journal of Health Sciences, 6(S8), 4138–4149. https://doi.org/10.53730/ijhs.v6nS8.13124

Issue

Section

Peer Review Articles