Abstract
Microwave assisted synthesis in organic chemistry is an important and a well established area of research due to a number of advantages over conventional heating methods. Further, nitrogen heterocycles of different ring sizes, with different substitution patterns and embedded in various molecular frameworks constitute extremely important structure classes in the search for bioactivity. Many compounds bearing five-membered heterocyclic rings in their structure have an extensive spectrum of pharmacological activities. Among them oxadiazoles and their derivatives have attracted considerable interest in material and medicinal chemistry as surrogates of carboxylic acids, esters and carboxamides. The various oxadiazole compounds have shown a wide array of biological activities in both agrochemical and pharmaceutical fields. The formation of this biologically important heterocyclic system under microwave conditions is described in this chapter.
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References
Kasi SV, Raja TK (2006) A rapid microwave assisted claisen rearrangement of 4-allyloxy-2-methylquinolines under solvent free condition. Ind J Heterocycl Chem 16:195–196
Omar FA, Mahfouz NM et al (1996) Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 31:819–825
Zarghi A, Hajimahdi Z et al (2008) Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents. Chem Pharm Bull 56:509–512
Mayekar AN (2010) Synthesis and antimicrobial studies on new substituted 1,3,4-oxadiazole derivatives bearing 6-bromonapthalelene moiety. Int J Chem 2:38–54
Zheng X, Li Z et al (2003) Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. J Fluorine Chem 123:163–169
Li Y, Liu J et al (2006) Stereoselective synthesis and fungicidal activities of (E)-α-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring. Bioorg Med Chem Lett 16:2278–2282
Ilango K, Valentina P et al (2009) Synthesis and characterization of 2,5-disubstituted-1,3,4-oxadiazoles as potential anti-inflammatory agents. J Young Pharm 1:72–76
Rastogi N, Singh VR et al (2006) Microwave mediated aminomethylation and antileishmanial activity of 2-{4’-(2”,4”-dichlorobenzyloxy)-phenyl}-1,3,4-oxadiazolin-5-thiones and 3-{4’-(2”,4”-dichlorobenzyloxy)phenyl}-4-phenyl-1,2,4-triazolin-5-thiones. Ind J Heterocycl Chem 16:5–8
Mishra P, Joshi GK, Shakya AK et al (1992) Pharmacological screening of few new 2-(substituted acetyl) amino-5-alkyl-1,3,4-oxadiazoles. Indian J Physiol Pharmacol 36:247–250
Sengupta P, Kumar DD et al (2008) Evaluation of anticancer activity of some 1,3,4-oxadiazole derivatives. Ind J Chem 47B:460–462
Swain CJ, Baker R et al (1991) Novel 5-HT3 antagonists. Indole oxadiazoles. J Med Chem 34:140–151
Orlek BS, Blaney FE et al (1991) Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor. J Med Chem 34:2726–2735
Tully WR, Gardner CR et al (1991) 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1, 2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors. J Med Chem 34:2060–2067
Ghani U, Ullah N (2010) New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site. Bioorg Med Chem 18:4042–4048
Han D, Meng XB et al (2009) Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism. Tetrahedron Asymmetry 20:399–410
Tandon VK, Chhor RB (2001) An efficient one pot synthesis of 1,3,4-oxadiazoles. Synth Commun 31:1727–1732
Jedlovska E, Lesko J (1994) A simple one-pot procedure for the synthesis of 1,3,4-oxadiazoles. Synth Commun 24:1879–1885
Sangshetti JN, Chabukswar AR et al (2011) Microwave assisted one-pot synthesis of some novel 2,5-disubstituted 1,3,4-oxadiazoles as antifungal agents. Bioorg Med Chem Lett 21:444–448
Rostamizadeh S, Ghaieni HR et al (2010) Clean one-pot synthesis of 1,2,4-oxadiazoles under solvent-free conditions using microwave irradiation and potassium fluoride as catalyst and solid support. Tetrahedron 66:494–497
Kidwai M, Goel Y (1996) Microwave induced novel synthetic route to organomercurials. Polyhedron 15:2819–2824
Brain CT, Paul JM et al (1999) Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Lett 40:3275–3278
Wang X, Li Z et al (2001) Synthesis of 2-(4-chlorobenzoylamido)-5-aryloxymethyl-1,3,4-oxadiazoles under microwave irradiation. Synth Commun 31:1907–1911
Bentiss F, Lagrenee M et al (2001) Rapid synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under microwave irradiation. Synth Commun 31:935–938
Maslat AO, Abussaud M et al (2002) Synthesis, antibacterial, antifungal and genotoxic activity of bis-1,3,4-oxadiazole derivatives. Polish J Chem 54:55–59
Joshi S, Karnik AV (2002) Facile conversion of acyldithiocarbazinate salts to 1,3,4-oxadiazole derivatives under microwave irradiation. Synth Commun 32:111–114
Mashraqui SH, Ghadigaonkar SG et al (2003) An expeditious and convenient one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles. Synth Commun 33:2541–2545
Rostamizadeh S, Housaini SAG (2004) Microwave assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles. Tetrahedron Lett 45:8753–8756
Khan KM, Zia-Ullah et al (2004) Microwave-assisted synthesis of 2,5-disubstituted-1,3,4-oxadiazoles. Lett Org Chem 1:50–52
Rao VS, Sekhar KVGC (2004) Iodobenzene diacetate mediated solid-state synthesis of heterocyclyl-1,3,4-oxadiazoles. Synth Commun 34:2153–2157
Li Z, Yu J et al (2004) Microwave accelerated solvent-free synthesis of 1,3,4-oxadiazoles using polymer supported dehydration reagent. Synth Commun 34:2981–2986
Natero R, Koltun DO et al (2004) Microwave-assisted one-step synthesis of substituted 2-chloromethyl-1,3,4-oxadiazoles. Synth Commun 34:2523–2529
Khan MTH, Choudhary MI et al (2005) Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. Bioorg Med Chem 13:3385–3395
Baxendale IR, Leya SV et al (2005) The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating. Tetrahedron 61:5323–5349
Wang Y, Sauer DR et al (2006) A simple and efficient one step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating. Tetrahedron Lett 47:105–108
Li Z, Xing Y et al (2006) Microwave-assisted expeditious synthesis of novel carbazole-based 1,3,4-oxadiazoles. Synth Commun 36:3285–3287
Frank PV, Girish KS et al (2007) Solvent-free microwave-assisted synthesis of oxadiazoles containing imidazole moiety. J Chem Sci 119:41–46
Saeed A (2007) An expeditious, solvent-free synthesis of some 5-aryl-2-(2-hydroxyphenyl)-1,3,4-oxadiazoles. Chem Heterocycl Compd 43:1072–1075
Polshettiwar V, Varma RS (2008) Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. Tetrahedron Lett 49:879–883
Pore DM, Mahadik SM et al (2008) Trichloroisocyanuric acid-mediated one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles at ambient temperature. Synth Commun 38:3121–3128
Singh S, Pandey OP et al (2009) Microwave assisted synthesis, spectroscopy and biochemical aspects of lanthum (III) and praseodymium (III) complexes with oxadiazole functionalized dithiocarbazinates. J Rare Earths 27:698–704
Han D, Meng XB et al (2009) Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism. Tetrahedron Asymmetr 20:399–410
Wang LN, Han D et al (2009) Microwave-assisted efficient synthesis of glucose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives catalyzed by sodium acetate. Carbohydr Res 344:2113–2119
Efimova YA, Karabanovich GG et al (2009) Tetrazoles: LV. Perparation of 2-anilino-5-aryl(hetaryl)-1,3,4-oxadiazoles from 5-substituted tetrazoles under microwave activation. Russ J Org Chem 45:1241–1243
Xu J, Wang DL et al (2009) Microwave-assisted synthesis and antifungal activity of 2,5-disubstituted-1,3,4-oxadiazoles containing azulene moiety. Synth Commun 39:2196–2204
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Rauf, A., Farshori, N.N. (2012). Oxadiazoles. In: Microwave-Induced Synthesis of Aromatic Heterocycles. SpringerBriefs in Molecular Science(), vol 3. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-1485-4_5
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DOI: https://doi.org/10.1007/978-94-007-1485-4_5
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