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Synthesis and characterization of 3-aryl[1,2,3,5]tetrazino[5,4-a]benzimidazole-4(3H)-thione derivatives

Vinita Sahu

Abstract


A series of 3-aryl[1,2,3,5]tetrazino[5,4-a]benzimidazole-4(3H)-thione derivatives have been synthesized. The compounds were synthesized in excellent yields (65-75%) and the structures were established on the basis of corresponding IR, 1H NMR, Mass and elemental analysis data. The purity has been ascertained on the basis of chromatographic resolution using CH2Cl2 as eluent. 


Keywords


3-aryl[1,2,3,5]tetrazino[5,4-a]benzimidazole-4(3H)-thione, Synthesis, Derivatives, Medicinal use, Energetic

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Devaraj NK, Weissleder R, Hilderbrand SA: Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging. Bioconjugate Chem. 2008,19: 2297.

Newell M, Ingram JD, Easun TL, Vickers SJ, Adams H, Ward MD, Thomas JA: Structure and Properties of Dinuclear [RuII([n]aneS4) Complexes of 3,6-bis(2-pyridyl)-1,2,4,5- Tetrazine. Inorg. Chem. 2006, 45:821. (b) Remenyi C, Reviakine R, Kaupp M: Density functional study of EPR parameters and spin density distributions of dicopper(I) complexes with bridging azo and tetrazine radical anion ligands. J. Phys. Chem. A 2006, 110:4021.

Gomez-Bengoa E, Helm MD, Plant A, Harrity JPA. The Participation of Alkynylboronates in Inverse Electron Demand [4 + 2] Cycloadditions: A Mechanistic Study. J. Am. Chem. Soc. 2007, 129:2691.

Boger DL, Zhang M: Total synthesis of (+-)-cis and (+-)-trans-Trikentrin A: Diels-Alder reactions of heteroaromatic azadienes. J. Am. Chem. Soc. 1991, 113:4230.

Wei T, Zhu W, Zhang X, Li YF, Xiao H: Molecular Design of 1,2,4,5-Tetrazine-Based High-Energy Density Materials. J. Phys. Chem. A 2009, 113:9404.

Blackman ML, Royzen M, Fox JM: Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. J. Am. Chem. Soc. 2008, 130:13518.

Del Bene JE, Alkorta I, Elguero J: Probing 1J(C-F) and nJ(F-F) Spin-spin Coupling Constants for Fluorazines: An Ab Initio Theoretical Investigation. J. Phys. Chem. A 2010, 114:2637.

Farago J, Novak Z, Schlosser G, Csampai A, Kotschy A: The azaphilic addition of organometallic reagents on tetrazines: scope and limitations. Tetrahedron 2004, 60:1991.

Zhu Y, Wu C, Li H, Zou X, Si X, Hu F, Yang H: Design, synthesis, and quantitative structure−activity relationship study of herbicidal analogues of pyrazolo[5,1-d][1,2,3,5] tetrazin-4(3H)-ones. J. Agric. Food Chem. 2007, 55:1364.

Novak Z, Kotschy A: The first cross-coupling reactions on tetrazines. Org. Lett. 2003, 5:3495. (b) Sammelson RE, Olmstead MM, Haddadin MJ, Kurth MJ: 1,2,4,5-Tetrazines as Oxidant and Reactant with DBU: An Unexpected Formation of a Novel Fused Tetraheterocyclic Azepine. J. Org. Chem. 2000, 65:9265.

Jordan BJ, Pollier, MA, Miller LA, Tiernan C, Clavier G, Audebert P, Rotello VM: Redox-Modulated Recognition of Tetrazines Using Thioureas. Org. Lett. 2007, 9:2835.

Hamasaki A, Ducray R, Boger DL: Two novel 1,2,4,5-tetrazines that participate in inverse electron demand Diels-Alder reactions with an unexpected regioselectivity. J. Org. Chem. 2006, 71:185. (b) Hoogenboom R, Moore BC, Schubert US: Microwave-assisted synthesis of 3,6-di(2-pyridyl)pyridazines: Unexpected ketone and aldehyde cycloaddition reactions. J. Org. Chem. 2006, 71:4903.

Heppekausen J, Klapo¨tke TM, Sproll SM : Synthesis of Functionalized Tetrazenes as Energetic Compounds. J. Org. Chem. 2009, 74:2460. (b) Domingo LR, Picher MT, Sa´ez JA: Toward an Understanding of the Unexpected Regioselective Hetero-Diels−Alder Reactions of Asymmetric Tetrazines with Electron-Rich Ethylenes: A DFT Study. J. Org. Chem. 2009, 74:2726.

Lodewyk MW, Kurth MJ, Tantillo DJ: Mechanisms for Formation of Diazocinones, Pyridazines, and Pyrazolines from Tetrazines—Oxyanion-Accelerated Pericyclic Cascades? J. Org. Chem. 2009, 74: 4804.

Bostai B, Novak Z, Benyei AC, Kotschy A: Quinoidal Tetrazines: Formation of a Fascinating Compound Class. Org. Lett. 2007, 9:3437.

Vivat JF, Adams H, Harrity JPA: Ambient Temperature Nitrogen-Directed Difluoroalkynylborane Carboni−Lindsey Cycloaddition Reactions. Org. Lett. 2010, 12:160.

Bidan G, Divisia-Blohorn B, Lapkowski M, Kern JM, Sauvage JP: Electroactive films of polypyrroles containing complexing cavities preformed by entwining ligands on metallic centers. J. Am. Chem. Soc. 1992, 114:5986.

Lang JP, Kawaguchi H, Tatsumi K: Synthesis of a Heterobimetallic Ladder Polymer [(η5-C5Me5)WS3Ag2Br]n. Inorg. Chem. 1997, 36:6447.

Audebert P, Saoud M, Miomandre F, Sadki S, Vernière MC, Hapiot P: Synthesis of new substituted tetrazines: electrochemical and spectroscopic properties. New J. Chem. 2004, 28:387.

Audebert P, Miomandre F, Sadki S, Clavier G : First example of an electroactive polymer issued from an oligothiophene substituted tetrazine. Electrochem. Commun. 2004, 6 :144.

Chavez DE, Hiskey MA: 1,2,4,5-tetrazine based energetic materials. J. Energ. Mater. 1999, 17: 357.

Chavez DE, Gilardi RD, Hiskey MA: 3,3′-Azobis(6-amino-1,2,4,5-tetrazine): A Novel High-Nitrogen Energetic Material. Angew. Chem. Int. Ed. 2000, 39:1791.

Chavez DE, Hiskey MA: Synthesis of the bi-heterocyclic parent ring system 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazine and some 3,6-disubstituted derivatives. J. Heterocycl. Chem. 1998, 35:1329.

Boger DL, Sakya SM: Inverse electron demand Diels-Alder reactions of 3,6-bis(methylthio)-1,2,4,5-tetrazine. 1,2-Diazine introduction and direct implementation of a divergent 1,2,4,5-tetrazine .fwdarw. 1,2-diazine .fwdarw. benzene (indoline/indole) Diels-Alder strategy. J. Org. Chem. 1988, 53:1415.

Hu WX, Rao GW, Sun YQ: Synthesis and antitumor activity of s-tetrazine derivatives. Bioorg. Med. Chem. Lett. 2004, 14:1177.

Clark AS, Deans B, Stevens MFG, Tisdale MJ, Wheelhouse RT, Denny BJ, Hartley JA: Antitumor Imidazotetrazines. 32.1 Synthesis of Novel Imidazotetrazinones and Related Bicyclic Heterocycles To Probe the Mode of Action of the Antitumor Drug Temozolomide. J. Med. Chem. 1996, 38:1493. (b) Denny BJ, Wheelhouse RT, Stevens MFG, Tsang LLH, Slack JA: NMR and Molecular Modeling Investigation of the Mechanism of Activation of the Antitumor Drug Temozolomide and Its Interaction with DNA. Biochemistry 1994, 33:9045.

Almerico AM, Mingoia F, Diana P, Barraja P, Lauria A, Montalbano A, Cirrincione G, Dattolo G: 1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones. Design, synthesis, and biological activity of new antitumor agents. J. Med. Chem. 2005, 48:2859.

Yates P, Merez O: Formation of dihydro- -tetrazines by the reaction of α-diazo ketones with bases. Tetrahedron lett. 1967,1:77.

Pinner A: Ueber die Einwirkung von Hydrazin auf Imidoäther. Ann. Chem. 1897, 297: 221.

Neilson DG, Roger R, Heatlie JWM, Newlands LR: Chemistry of amidrazones. Chem. Rev. 1970,70:151.

Pilgram K, Skiles RD: Unsymmetrically 3,6-disubstituted s-tetrazines. Synthesis of 3-aryl-6-(perfluoroalkyl)-1,2,4,5-tetrazines and 1,2-dihydro derivatives. J.Org. Chem. 1976,41:3392.




DOI: http://dx.doi.org/10.14259%2Fbmc.v1i2.74

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