Review on Types of Three Components Reactions
DOI:
https://doi.org/10.46243/jst.2020.v5.i5.pp01-09Keywords:
mannich reaction, sulfazane reactionAbstract
This review described the three-component chemical reactions, their types, how they got there, and their importance in preparing compounds that have biological and pharmaceutical significance and in other magazines of chemistry. Among them are the enamin-mannich reactions, the formazane reactions, the sulfazane, and some annular closure reactions.Three-component interaction is included in the preparation of the pharmaceutical compounds, as they need the shortest steps and the fastest results, so such interactions are used in the preparation of many drugs and the simplest examples are tramadol and some anesthetics used in surgical processes. Keywords: mannich reaction, mannich reaction, sulfazane reaction, sulfazane reaction
References
Peter W. Atkins, Julio de Paula: PhysikalischeChemie. 4. Auflage, Wiley-VCH,Weinheim 2006, ISBN 978-3-527-31546-8, S. 106–108
Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A. Synthesis and anticonvulsant activity of new 2 substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg Med ChemLett. 2004;14:6057–6059. doi: 10.1016/j.bmcl.2004.09.072
Al-Soud YA, Al-Dweri MN, Al-Masoudi NA. Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives. Farmaco. 2004;59:775–783. doi: 10.1016/j.farmac.2004.05.006. [PubMed] [CrossRef] [Google Scholar]
Mieaad M, NaghamMahmoodAljamali, WassanAlaShubber., Sabreen Ali Abdalrahman."New Azomethine-Azo Heterocyclic Ligands Via Cyclization of Ester".,Research Journal of Pharmacy and Technology,.2018,(11),6. 2555- 2560., DOI : 10.5958/0974-360X.2018.00472.9
Bailey EM, Krakovsky DJ, Rybak M. The triazole antifungal agents: a review of itraconazole and fluconazole. Pharmacotherapy. 1990;10:146–
Bourgeois I, Pestel-Caron M, Lemeland JF, Pons JL, Caron F. Tolerance to the glycopeptidesvancomycin and teicoplanin in coagulase negative Staphylococci. Antimicrob Agents Chemother. 2007;51(2):740–743. doi: 10.1128/AAC.00719-06
NaghamMahmoodAljamali.; Intisar O A. "Synthesis of Sulfur Heterocyclic Compounds and Study of Expecte d Biological Activity",Research J. Pharm. and Tech., 2015, 8,9,1225-1242, DOI: 10.5958/0974-360X.2015.00224.3
Clemons M, Coleman RE, Verma S. Cancer Treat Rev. 2004;30:325–332. doi: 10.1016/j.ctrv.2004.03.004. [PubMed] [ CrossRef] [Google Scholar]
CLSI (2008) Performance standards for antimicrobial susceptibility testing; Eighteenth International Supplement. CLSI document M7-MIC. Clinical Laboratory Standards Institute, Wayne
AfaeqgaberKadem, Ahmed Adnan Abdul Hussein, NaghamMahmoodAljamali,Ahmed A A H, Afaq J K. (2020)., Invention of Imidazole &Thiazole-Sulfazane Ligands (Synthesis, Spectral Investigation, Microbial Behavior) for The First Time., Int. J. Pharm. Res., Vol. 12
NaghamMahmoodAljamali., "The Various Preparation Methods in Synthetic C hemistry".,1Edt.,Evincepub Publishing house, 2019., ISBN :978-93-88277-82-2
NaghamMahmoodAljamali. "Reactions and Mechanisms".,1 Edt., IJMRA Publication,2018.,ISBN : 978- 93-87176-25-6
NaghamMahmoodAljamali."Experimental Methods for Preparation of MannichBases,Formazan, Normal and Cyclic Sulfur Compounds ", 1 st edition Evince pub Publishing House;2018, ISBN: 978-93-87905-19-1
NaghamMahmoodAljamali. 2016. "Synthesis and Biological Study of Hetero (Atoms and Cycles) Compounds", Der PharmaChemica, 8,6, 40-48
Alea JK, JelalHasen Mohamed, NaghamMahmoodAljamali., Thiazole Amide Derivatives (Synthesis, Spectral Investigation, Chemical Properties, Antifungal Assay)., NeuroQuantology, 2020, 18, 1,Page 16-25., doi: 10.14704/nq.2020.18.1.NQ20102
Metwally N.H. A simple green synthesis of (Z) -5-arylmethylene-4-thioxothiazolidines and thiopyrano[2,3-d]thiazolidine-2-thiones in PEG-400 under catalyst-free conditions. J. Sulfur Chem. 2014;35:528–537. doi: 10.1080/17415993.2014.933341. [CrossRef] [Google Scholar]
Lozynskyi A., Zimenkovsky B., Lesyk R. Synthesis and Anticancer Activity of New Thiopyrano[2,3-d]thiazoles Based on Cinnamic Acid Amides. Sci. Pharm. 2014;82:723–733. doi: 10.3797/ scipharm.1408-05. [PMC free article] [PubMed] [CrossRef] [Google Scholar]
Lozynskyi A., Zasidko V., Atamanyuk D., Kaminskyy D., Derkach H., Karpenko O., Ogurtsov V., Kutsyk R., Lesyk R. Synthesis, an tioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids. Mol. Divers. 2017;21:427–436. doi: 10.1007/s11030- 017-9737-8
Lozynskyi A., Zimenkovsky B., Nektegayev I., Lesyk R. Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds. Heterocycl. Commun. 2015;21:55–59. doi: 10.1515/hc-2014-0204. [CrossRef] [Google Scholar]
Imad Kareem AlwanAlsabri, HasaneenKudhairAbdullabass,NaghamMahmoodAljamali, Imad K A A, Hasaneen K A., Invention o f (Gluta.Sulfazane-Cefixime) Compounds as Inhibitors of Cancerous Tumors., Journal of Cardiovascular Disease Research, 2020,11, 2., 44-55., DOI: 10.31838/jcdr.2020.11.02.09
AseelMahmoodJawad, NaghamMahmoodAljamali, SaherMahmoodJwad, Aseel M J, Saher M J., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology,2020,14, 2, p:1115-1122
NaghamMahmoodAljamali, Nemah Sahib Mohammed, Spectral Studying and Chemical Properties of (Imine and Formazan) -Ligands with Some Complexes with Zinc (Zn2+), Journal of Natural Sciences Research, 2016, 6 (11), 16-25
Demirbas A, Sahin D, Demirbas N, Karaoglu SA. Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Eur J Med Chem. 2009;44:2896–2903. doi: 10.1016/j.ejmech.2008.12.005
Dobosz M, Pachuta-Stec A. Cyclization of 1-cyanoacetyl-4-substituted thiosemicarbazides to 1,2,4-triazole or 1,3,4-thiadiazole derivatives. Acta Pol Pharm. 1995;52:103–111. [Google Scholar]
Intisar O A, Nuha S S, Zainab M J,NaghamMahmoodAljamali,"Synthesis of New Organic Compounds Via Three Components Reaction with Studying of (Identification,Thermal Behavior, Bioactivity on Bacteria of Teeth)".,Journal of Global Pharma Technology. 2017;11,9,157-164
NaghamMahmoodAljamali, Imad Kareem AlwanAlsabri., Development of Trimethoprim Drug and Innovation of Sulfazane-Trimethoprim Derivatives as Anticancer Agents., Biomedical & Pharmacology Journal, March 2020., Vol. 13, (2), p. 613-625., http://dx.doi.org/10.13005/bpj/1925. Review on Types of Three Components Reactions _____________________________________________________________________________________________________________________________ ______________ 8 | Page
Dobosz M, Pitucha M, Wujec M. The reactions of cyclization of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system. Acta Pol Pharm. 1996;53:31–38
Dogan HN, Duran A, Rollas S, Sener G, Uysal MK, Gülen D. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities. Bioorg Med Chem. 2002;10:2893–2898. doi: 10.1016/S0968-0896(02)00143-8
NaghamMahmoodAljamali.,"(Synthesis,Investigation,Chromatography,Thermal)-Behavior of (Five,Seven)- Membered Ring with Azo and Anil Compounds".,Pak. J. Biotechnol. Vol. 15,1, 219-239, (2018)
Metwally N.H. Synthesis of some new fused thiopyrano[2,3-d]thiazoles and their derivatives. J. Sulfur Chem. 2007;28:275–284. d oi: 10.1080/17415990701299468
NaghamMahmoodAljamali, (2015). Review in Azo Compounds and its Biological Activity. Biochem Anal Biochem,4, 169., doi:10.4172/2161- 1009.1000169
Heir chfft,Noorhan Ali Hamza, NourAlhuda Abdul Abbas Bahar,NaghamMahmoodAljamali., 2019,Nitrophenyl Hydrazine Derivatives (Formation, Characterization, Physical and Polarized Optical Behavior).,Jour of Adv Research in Dyna mical & Control Systems, Vol. 11, No. 5, 206-213
Duran A, Dogan HN, Rollas S. Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H- 1,2,4-triazoline-5-thiones. Farmaco. 2002;57:559–564. doi: 10.1016/S0014-827X(02)01248-X
El Shehry MF, Abu-Hashem AA, El-Telbani EM. Synthesis of 3 -((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur J Med Chem. 2010;45:1906–1911. doi: 10.1016/j.ejmech.2010.01.030
Gadad AK, Noolvi MN, Karpoormath RV. Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo-[2,1-b]-1,3,4-thiadiazole derivatives. Bioorg Med Chem. 2004;12:5651–5659. doi: 10.1 016/j.bmc.2004.07.060. [PubMed] [CrossRef] [Google Scholar]
Gülerman NN, Doğan HN, Rollas S, Johansson C, Çelik C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4 triazoline-3-thiones and their antimicrobial activities. Farmaco. 2001;56:953–958. doi: 10.1016/S0014-827X(01)01167-3
NaghamMahmoodAljamali, AseelMahmoodJawad, AseelFadhil K, NourAlhuda Abdul Abbas Bahar,Nour A AA. (2019). Review in Chemical Structures of Common Compounds. International Journal of Chemical Synthesis and Chemical Reactions.; 5 (1) 1–15p
NaghamMahmoodAljamali., 2015. Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)".,Research J. Pharm. and Tech, 8,1, 78-84., DOI: 10.5958/0974-360X.2015.00016.5
Zelisko N., Karpenko O., Muzychenko V., Gzella A., Grellier P., Lesyk R. trans-Aconitic acid-based hetero-Diels-Alder reaction in the synthesis of thiopyrano[2,3-d][1,3]thiazole derivatives. Tetrahedron Lett. 2017;58:1751–1754. doi: 10.1016/j.tetlet.2017.03.062. [CrossRef] [Google Scholar]
Zelisko N.I., Finiuk N.S., Shvets V.M., Medvid Y.O., Stoika R.S., Lesyk R.B. Screening of spi ro-substituted thiopyrano[2,3-d]thiazoles for their cytotoxic action on tumor cells. Biopolym. Cell. 2017;33:282–290. doi: 10.7124/bc.00095A
Mestaf M, NawfelMuhammedBaqerMuhsin., NeuroQuantology, 2019.,17 (11), 11-16., 10.14704/nq.2019. 17.11.NQ19108
MiadMohmed,NaghamMahmoodAljamali,Sabreen Ali Abdalrahman.,WassanAlaShubber., "Formation of Oxadiazole Derivatives Ligands from Condensation and Imination Reaction with References To Spectral Investigation, Thermal and Microbial Assay"., Biochem. Cell. Arch., 2018,18, 1, pp. 847-853
Harish K, Sadique AJ, Suroor AK, Mohammad A. 1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties. Eur J Med Chem. 2008;43:2688–2698. doi: 10.1016/j.ejmech.2008.01.039
AseelMahmoodJawad, NaghamMahmoodAljamali, Aseel M J.,"Innovation, Preparation of Cephalexin Drug Derivatives and Studying of (Toxicity & Resistance of Infection)"., International Journal of Psychosocial Rehabilitation, Vol. 24, Issue 04, 2020, 3754-3767.,DOI: 10.37200/IJPR/V24I4/PR201489
NaghamMahmoodAljamali.,Synthesis of Antifungal Chemical Compounds from Fluconazole with (Pharma-Chemical) Studying, Research journal of Pharmaceutical, biological and chemical sciences, 2017, 8 (3), 564-573
Holmwood G, Buechel KH, Plempel M, Haller J (1982) Antimicrobial azoles. ChemAbstr 96:62979s. Patent RFN DE 3018865, 1981
Kaplaushenko AH, Panasenko OI, Knish EH, Scherbina RO. Synthesis, physicochemical and biological properties of 2 -(5-R1-4-R2-1,2,4-triazol- 3-ylthio)acetic acids. Farm Zh. 2008;2:67–72
Klimešová V, Zahajská L, Waisser K, Kaustová J, Möllmann U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Farmaco. 2004;59:279–288. doi: 10.1016/j.farmac.2004.01.006
Kumar D, Kumar NM, Chang K-H, Shah K. Synthesis and anticancer activity of 5 -(3-indolyl)-1,3,4-thiadiazoles. Eur J Med Chem. 2010;45:4664–4668. doi: 10.1016/j.ejmech.2010.07.023
AseelMahmoodJawad,Mostafa N. Mohamed Salih, NaghamMahmoodAljamali, Thanaa A. H,Nadia H O. Review on Chalcone (Preparation,Reactions, Medical and Bio Applications). International Journal of Chemical Synthesis and Chemical Reactions.; 2019,5,(1):16–27p
NawfelMuhammedBaqerMuhsin,Hayder H K, Noor H D, NaghamMahmoodAljamali., "Preparation of Chemical Inhibitors to Treat the Corrosion and Erosion of Machines", International Journal of Engineering, Applied and Management Sciences Paradigms.,2019, 54,3,89-93
Liesen AP, De Aquino TM, Carvalho CS, Lima VT, De Araújo JM, De Lima JG, De Faria AR, De Melo EJT, Alves AJ, Alves EW, Alves AQ, Góes AJS. Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of t hiosemicarbazides, 4-thiazolidinones and 1,3,4 thiadiazoles. Eur J Med Chem. 2010;45:3685–3691. doi: 10.1016/j.ejmech.2010.05.017
McGinnis MR, Pasarell L, Sutton DA, Fothergill AW, Cooper CR, Rinaldi MG. Antimicrob Agents Chemother. 1997;41:1832–1834
Oxford Diffraction, Xcalibur CCD System (2006) CrysAlis Software System, Version 1.171. Oxford Diffraction Ltd., Abingdon
Padmavathi V, Sudhakar Reddy G, Padmaja A, Kondaiah P, Ali-Shazia Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem. 2009;44:2106–2112. doi: 10.1016/j.ejmech.2008.10.012. [PubMed] [CrossRef] [Google Scholar]. 9 | Page
Meaad M,NaghamMahmoodAljamali,Nadheema A A.,"Preparation,Spectral Investigation, Thermal Analysis, Biochemical Studying of New (Oxadiazole-Five Membered Ring)-Ligands".,Journal of Global Pharmacy Technology,2018;10,1,20-29
Ramasubbu N, Parthasarathy R. Short S…O contacts: structure of 2,5-bis(p-methoxyphenylhydroxymethyl)thiophene. ActaCrystallogr C. 1989;45:457–460. doi: 10.1107/S0108270188010728
NaghamMahmoodAljamali, Rabab Mahdi UbaidMahmood, RanaNeamaAtiya,Fatimah A.Wannas, Rabab M U M. Review on preparation methods & application fields of oxadiazole., International Journal of Chemical Synthesis and Chemical Reactions, 2020, 6, 1
Sheldrick GM. A short history of SHELX. ActaCrystallogr A. 2008;64:112–122. doi: 10.1107/S0108767307043930
Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, KalyanChA, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M. Synthesis of new S-derivatives of clubbed triazolylthiazole as anti-Mycobacterium tuberculosis agents. Bioorg Med Chem. 2007;15:3997–4008. doi: 10.1016/j.bmc.2007.04.003
Siwek A, Paneth P. Computational studies of the cyclization of thiosemicarbazides. J Phys Org Chem. 2007;20:463–468. doi: 10.1002/poc.1179
Siwek A, Wujec M, Dobosz M, Wawrzycka-Gorczyca I. Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides. Heteroat Chem. 2010;21(7):521–532. doi: 10.1002/hc.20643
NaghamMahmoodAljamali, Rabab Mahdi UbaidMahmood,Radhiyah Abdul BaqiAldujaili, RanaNeamaAtiya. Review on Preparation and Application Fields of Triazole&Tetrazole Derivatives.International Journal of Analytical and Applied Chemistry. 2020; 6(1): 50–60p
Ulusoy N, Gürsoy A, Ötük G. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco. 2001;56:947–952. doi: 10.1016/S0014-827X(01)01128-4
Wei Q-L, Zhang S-S, Gao J, Li W-H, Xu L-Z, Yu Z-G. Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents. Bioorg Med Chem. 2006;14:7146–7153. doi: 10.1016/j.bmc.2006.06.065
White EL, Suling WJ, Ross LJ, Seitz LE, Reynolds RC. 2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ. J AntimicrobChemother. 2002;50:111–114. doi: 10.1093/jac/dkf075. [PubMed] [CrossRef] [Google Scholar]
Wilson AJC, editor. International tables for crystallography. Dordrecht: Kluwer Academic Publishers; 1995. [Google Scholar]
Wujec M, Paneth P. Mechanism of 4-methyl-1,2,4-triazol-3-thiole reaction with formaldehyde. A DFT study. J Phys Org Chem. 2007;20:1043–1049. doi: 10.1002/poc.1250
Polovkovych S.V., Karkhut A.I., Marintsova N.G., Lesyk R.B., Zimenkovsky B.S., Novikov V.P. Synthesis of New Schiff Bases and Polycyclic Fused Thiopyranothiazoles Containing 4,6-Dichloro-1,3,5-Triazine Moiety. J. Heterocycl. Chem. 2013;50:1419–1424. doi: 10.1002/jhet.890
Metwally N.H. A convenient synthesis o f some new 5-substituted-4-thioxo-thiazolidines and fused thiopyrano[2,3-d]thiazole derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2008;183:2073–2085. doi: 10.1080/10426500701849105




