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A new convenient synthesis of 5-aryl-2-(arylamino)-1,3,4-oxadiazole derivatives

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Abstract

Electrical energy offers numerous benefits for conducting a synthesis, including increased reaction rates, yield enhancements and cleaner chemistries. 5-Aryl-2-(arylamino)-1,3,4-oxadiazoles were synthesised directly from acylthiosemicarbazide on the platinum electrode under controlled potential electrolysis in an undivided cell assembly in acetonitrile.

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References

  • Brain, C. T., & Brunton, S. A. (2001). Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents. Synlett, 2001, 382–384. DOI: 10.1055/s-2001-11404.

    Google Scholar 

  • Brain, C. T., Paul, J. M., Loong, Y., & Oakley, P. J. (1999). Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Letters, 40, 3275–3278. DOI: 10.1016/s0040-4039(99)00382-2.

    Article  CAS  Google Scholar 

  • Brown, B. J., Clemens, I. R., & Neesom, J. K. (2000). Diisopropylcarbodiimide: A novel reagent for the synthesis of 1,3,4-oxadiazoles on solid-phase. Synlett, 2000, 131–133. DOI: 10.1055/s-2000-6454.

    Article  Google Scholar 

  • Coppo, F. T., Evans, K. A., Graybill, T. L., & Burton, G. (2004). Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents. Tetrahedron Letters, 45, 3257–3260. DOI: 10.1016/j.tetlet.2004.02.119.

    Article  CAS  Google Scholar 

  • Cesur, N., Birteksöz, S., & Ötük, G. (2002). Synthesis and biological evaluation of some new thiosemicarbazide, 4-thiazolidinone, 1,3,4-oxadiazole and 1,2,4-triazole-3-thione derivatives bearing imidazo[1,2-a]pyridine moiety. Acta Pharmaceutica Turcica, 44, 23–41.

    CAS  Google Scholar 

  • Chiba, T., & Okimoto, M. (1992). Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to Δ3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles. The Journal of Organic Chemistry, 57, 1375–1379. DOI: 10.1021/jo00031a014.

    Article  CAS  Google Scholar 

  • Fry, A. J. (1989). Synthetic organic electrochemistry (2nd ed., pp. 68–78). New York, NY, USA: Wiley.

    Google Scholar 

  • Golovlyova, S. M., Moskvichev, Y. A., Alov, E. M., Kobylinsky, D. B., & Ermolaeva, V. V. (2001). Synthesis of novel five-membered nitrogen-containing heterocyclic compounds from derivatives of arylsulfonyl- and arylthioacetic and -propionic acids. Chemistry of Heterocyclic Compounds, 37, 1102–1106. DOI: 10.1023/a:1013275515682.

    Article  CAS  Google Scholar 

  • Hetzheim, A., & Möckel, K. (1966). Recent advances in 1,3,4-oxadiazole chemistry. In A. R. Katritzky, & A. J. Boulton (Eds.), Advances in heterocyclic chemistry (Vol. 7, pp. 183–224). New York, NY, USA: Academic Press. DOI: 10.1016/s0065-2725(08)60591-7.

    Google Scholar 

  • Hill, J. (1984). 1,3,4-Oxadiazoles. In K. T. Potts (Ed.), Comprehensive heterocyclic chemistry (Vol. 6, Part 4B, Chapter 4.23, pp. 427–446). Oxford, UK: Pergamon Press. DOI: 10.1016/b978-008096519-2.00091-6.

    Chapter  Google Scholar 

  • Holla, B. S., Gonsalves, R., & Shenoy, S. (2000). Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes. European Journal of Medicinal Chemistry, 35, 267–271. DOI: 10.1016/s0223-5234(00)00154-9.

    Article  CAS  Google Scholar 

  • Kilburn, J. P., Lau, J., & Jones, R. C. F. (2001). 1,3,4-Oxadiazole formation; a novel solid support strategy. Tetrahedron Letters, 42, 2583–2586. DOI: 10.1016/s0040-4039(01) 00222-2.

    Article  CAS  Google Scholar 

  • Kumar, S. (2011). Synthesis and biological activity of 5-substituted-2-amino-1,3,4-oxadiazole derivatives. Turkish Journal of Chemistry, 35, 99–108. DOI: 10.3906/kim-0908-177.

    CAS  Google Scholar 

  • Ley, S. V., Baxendale, I. R., Bream, R. N., Jackson, P. S., Leach, A. G., Longbottom, D. A., Nesi, M., Scott, J. S., Storer, R. I., & Taylor, S. J. (2000). Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation. Journal of the Chemical Society, Perkin Transactions 1, 2000, 3815–4195. DOI: 10.1039/b006588i.

    Article  Google Scholar 

  • Liu, F. M, Wang, B. L, & Zhang, Z. F. (2001). Studies on 1-(2′-phenyl-1′,2′,3′-triazol-4′-formyl)-4-arylthiosemicarbazides and related heterocyclic compounds. Chinese Journal of Organic Chemistry, 21, 1126–1131.

    CAS  Google Scholar 

  • Mann, C. K., & Barnes, K. K. (1970). Electrochemical reactions in nonaqueous systems (pp. 13–18). New York, NY, USA: Marcel Dekker.

    Google Scholar 

  • Mohan, T. P., Vishalakshi, B., Bhat, K. S., Rao, K. S., & Kendappa, G. N. (2004). Synthesis and insecticidal activity of some 1,3,4-oxadiazole derivatives containing phenoxyfluorophenyl group. Indian Journal of Chemistry, Section B, 43B, 1798–1801.

    CAS  Google Scholar 

  • Omar, F. A., Mahfouz, N. M., & Rahman, M. A. (1996). Design, synthesis and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. European Journal of Medicinal Chemistry, 31, 819–825. DOI: 10.1016/0223-5234(96)83976-6.

    Article  CAS  Google Scholar 

  • Palaska, E., Şahin, G., Kelicen, P., Durlu, N. T., & Altinok, G. (2002). Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Il Farmaco, 57, 101–107. DOI: 10.1016/s0014-827x(01)01176-4.

    Article  CAS  Google Scholar 

  • Sharma, L. K., Kumar, S., Singh, S., & Singh, R. K. P. (2010). Electrochemical synthesis of 5-substituted-2-amino (substituted amino)-1,3,4-oxadiazoles at the platinum electrode. Russian Journal of Electrochemistry, 46, 34–40. DOI: 10.1134/s1023193510010040.

    Article  CAS  Google Scholar 

  • Shono, T. (Ed.) (1991). Electroorganic synthesis (Series: Best synthetic methods, pp. 11–19). London, UK: Academic Press.

    Google Scholar 

  • Zou, X. J., Lai, L. H., Jin, G. Y., & Zhang, Z. X. (2002a). Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. Journal of Agricultural and Food Chemistry, 50, 3757–3760. DOI: 10.1021/jf0201677.

    Article  CAS  Google Scholar 

  • Zou, X., Zhang, Z., & Jin, G. (2002b). Synthesis and biological activity of 1,3,4-oxadiazole-substituted pyridazinones. Journal of Chemical Research, 5, 228–230. DOI: 10.3184/030823402103171780.

    Article  Google Scholar 

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Correspondence to Sanjeev Kumar.

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Kumar, S. A new convenient synthesis of 5-aryl-2-(arylamino)-1,3,4-oxadiazole derivatives. Chem. Pap. 66, 216–220 (2012). https://doi.org/10.2478/s11696-011-0124-0

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