Abstract
A novel, facile and eco-compatible electrochemical synthesis of substituted bis-1,3,4-oxadiazoles have been carried out at platinum electrode via controlled potential electrocyclization of ethylenediacylthiosemicarbazone in the presence of acetonitrile as non-aqueous solvent and LiClO4 as supporting electrolyte. The reaction products were characterized by spectroscopic methods and mechanism was deduced with the help of cyclic voltammetry. The fungicidal activity of product 6a–6f was evaluated against fungal strain Aspergillus flavus and Alternaria solani. Excellent yields with high atom economy, shortest reaction time and easy work-up are attractive features in context to green chemistry.
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El-Emam A, Al-Deeb OA, Al-Omar M (2004) Synthesis, antimicrobial and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg Med Chem 12:5107–5113
Maslat AO, Abussaud M, Tashtoush H, Al-Talib M (2002) Synthesis, antibacterial, antifungal and genotoxic activity of bis-1,3,4-oxadiazole derivatives. Polish J Pharmacol 54:55–59
Kucukguzel SG, Oruc EE, Rollas S, Sahin F, Ozbek A (2002) Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 37:197–206
Chauhan D, Chauhan JS, Singh JS, Bajpai K, Joshi MN (2003) Synthesis and bioevaluation of some novel nucleosides as antiherptic agents. Indian J Chem 42B:215–218
Kagthara PR, Shah NS, Doshi RK, Parekh HH (1999) Synthesis of 2,5-disubstituted-1,3,4-oxadiazoles as biologically active heterocycles. Indian J Chem 38B:572–576
Mohan TP, Vishalakshi B, Bhat KS, Kendappa GN (2004) Synthesis and insecticidal activity of some 1,3,4-oxadiazole derivatives containing phenoxy fluoro group. Indian J Chem 43B:1798–1801
Kennedy DA, Summers LA (1981) Chemical constitution and activity of Herbicides: part XIV: Reduction potential and herbicidal activity of 4,4-(1,3,4-thiadiazoly-2,5-diyl) and 4,4-(1,3,4-oxadiazol-2,5-diyl) bis (1-methylpyridinium)diiodides. J Heterocycl Chem 18:401–410
Santagati M, Modica M, Santagati A, Russo F, Caruso A, Cutuli V (1994) Synthesis and pharmacological properties of benzothiazole, 1,3,4-oxadiazole and 1,2,4-thiadiazole derivatives. Pharmazie 49:880–884
Mullican MD, Kostlan CR, Schrier DJ, Dyer R (1993) Design of 5-(3,5-di-ter-butyl-4-hydroxyphenyl)-1,3,4-thiadiazol-1-yl-1,3,4-oxadiazoles and 1,2,4-triazoles as orally active, non ulcerogenic anti-inflammatory agents. J Med Chem 36:1090–1099
Yale HI, Losee K (1966) Design of 5-(3,5-di-ter-butyl-4-hydroxyphenyl)-1,3,4-thiadiazol-1-yl-1,3,4-oxadiazoles and 1,2,4-triazoles as orally active, non ulcerogenic anti-inflammatory agents. J Med Chem 9:478–483
Khan MS, Khan RM, Drabu S (2001) Anticonvulsant and antibacterial activity of some new 1,3,4-oxadiazole derivatives Indian. J Heterocycl Chem 11:119–122
Maillard J, Vincent M, Morin R, Bernard M (1962) Hypnotic and sedative drug, 2-(o-hydroxyphenyl)-1,3,4-oxadiazole. Chem Abstr 57:15251
Jessen KA, English NM, Wang JY, Maliartenou SK, Archer SP, Qiu L (2005) The discovery and mechanism of action of novel tumour-selective and apoptosis-inducing 3,5-diaryl-1,2,4-oxadiazole series using a chemical genetics approach. Mol Cancer Ther 4:761–771
Farghaly AA, Bekhit AA, Park JY (2000) Design and synthesis of some oxadiazolyl, thiazolidinyl and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory and antimicrobial agents. Arch Pharm 333:53–57
Dolman SJ, Gosselin F, O’Shea PD, Davies IW (2006) Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles. J Org Chem 71:9548–9551
Omar FA, Mafouz NM, Rahman MA (1996) Design, synthesis and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 31:819–825
Golovlyova S, Moskvichev M, Alov YA, Kobylinsky EM, Ermolaeva DB (2001) Synthesis of novel five membered nitrogen containing heterocyclic compounds from derivatives of arylsulfonyl and arylthioacetic and propionic acids. Chem Heterocycl Compd 37:1102–1106
Liu F, Wang B, Zhang Z (2001) Studies on 1-(2′-phenyl-1′,2′,3′-triazol-4′-formyl)-4-arylthiosemicarbazides and related heterocyclic compounds. Youji Huaxue 21:1126–1131
Hetzheim A, Moeckel K (1976) Recent advances in 1,3,4-oxadiazole chemistry. Adv Heterocycl Chem 7:183–224
Hill J (1984) Comprehensive heterocyclic chemistry, vol 6. Pergamon Press, Oxford, p 427
Wang X, Li Z, Yang J (2002) Synthesis of 2-(4-methoxylphenyloxy-acetylamido)-5-aryloxymethyl-1,3,4-oxadiazoles under microwave irradiation. Synth Commun 32:1097–1103
Cappo FT, Evans KA, Graybill TL, Burton G (2004) Efficient one pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin bound reagents. Tetrahedron Lett 45:3257–3260
Yoshida J, Kataoka K, Horcajada R, Nagaki A (2008) Oxidation and reductions in organic synthesis. Chem Rev 108:2265–2299
Singh S, Sharma LK, Saraswat A, Singh RKP (2012) Electrochemically initiated oxidative cyclization: a versatile route for the synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles. Montash Chem 143:1427–1430
Saraswat A, Sharma LK, Srivastava MK, Siddiqui IR, Singh RKP (2012) A novel electro-organic synthesis of aniline-based copolymers at platinum electrodes. J Appl Pol Sci 123(3):1479–1485
Saraswat A, Sharma LK, Singh S, Siddiqui IR, Singh RKP (2013) Chemoselective henry reaction catalyzed by electro-generated base. Res Chem Interm 39:1393–1399
Saraswat A, Sharma LK, Singh S, Singh RKP (2013) Electrochemical assisted synthesis and characterization of perchloric acid-doped aniline-functionalized copolymers. Synth Met 167:31–36
Sharma LK, Saraswat A, Singh S, Siddiqui IR, Singh RKP (2013) Anodic mediated synthesis and antifungal study of bis-1,3,4-oxadiazoles. J Indian Chem Soc 90(7):991–996
Singh S, Sharma LK, Saraswat A, Srivastav MK, Siddiqui IR, Singh RKP (2014) Anodic cyclization: a protocol for the synthesis of 2,5-disubstiuted-1,3,4-oxadiazoles. Chem Heterocycl Comp 49(10):1508–1514
Sharma LK, Singh S, Singh RKP (2011) Green synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles at the platinum anode in the acetic acid. Indian J Chem 50B:110–114
Sharma LK, Kumar S, Singh S, Singh RKP (2010) Electroorganic synthesis of 5-substituted-2-amino (substituted amino) 1,3,4-oxadiazoles at the platinum electrode. Electrokhimiya 46(1):37–42
Siddiqui IR, Singh PK, Singh J, Singh J (2003) Synthesis and fungicidal activity of novel 4,4′-bis(2-aryl-5-methyl/unsubstituted-4-oxo-thiazolidin-3-yl)bibenzyl. J Agric Food Chem 51:7062–7065
Singh S, Sharma LK, Saraswat A, Siddiqui IR, Kehri HK, Singh RKP (2013) Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents. RSC Adv 3:4237–4245
Acknowledgments
The authors thank the Head, Department of Chemistry, University of Allahabad for providing necessary facilities, Sophisticated Analytical Instrument Facility (SAIF) a division of CDRI (Central Drug Research Institute), Lucknow for spectra and UGC, New Delhi India for providing financial assistance.
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Sharma, L.K., Saraswat, A., Singh, S. et al. Electro-organic Mediated Synthesis of bis-1,3,4-Oxadiazoles and Evaluation of Their Antifungal Activity. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 85, 29–34 (2015). https://doi.org/10.1007/s40010-014-0175-z
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DOI: https://doi.org/10.1007/s40010-014-0175-z