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T3P as an efficient cyclodehydration reagent for the one-pot synthesis of 2-amino-1,3,4-oxadiazoles

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Abstract

A scalable and environmentally friendly one-pot method for the synthesis of 2-amino-1,3,4-oxadiazoles from acylhydrazides and isocyanates has been achieved with propane phosponic anhydride (T3P) acting as cyclodehydrating reagent.

A one-pot synthesis of 2-amino-1,3,4-oxadiazoles from acylhydrazides and isocyanates via cyclodehydration of the acyl semicarbazides, formed in situ, by T3P has been developed.

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References

  1. Bostrom J, Hogner A, Linas A, Wellner E and Plowright A 2012 J. Med. Chem. 55 1817

  2. (a) Nofal Z M, Fahmy H H and Mohamed H S 2002 Arch.Pharm. Res. 25 28; (b) Chapleo C B, Myers M, Saville J F, Smith A C B, Stilling M R, Tulloch I F, Walter D S and Welbourn A P 1986 J. Med. Chem. 292273; (c) Kiselyov A M M, Oprea T, Lemcke H, Weiss D G, Ikizalp N N, Kuznetsov S A and Semenov V V 2010 Eur. J. Med. Chem. 45 1683; (d) Yale H L and Losee K 1966 J. Med. Chem. 9 478; (e) Ghirian D, Schwatz I and Simiti I 1974 Farmacia 22 141

  3. (a) Zou X J, Lai L H, Jin G Y and Zhang Z X 2002 J. Agric. Food. Chem. 50 3757; (b) Chudgar N K, Shah S N and Vora R A 1989 Mol. Cryst. Lig. Cryst. 172 51

  4. Chekler E L P, Elokdah H M and Butera J 2008 Tetrahedron Lett. 49 6709

  5. Dolman S J, Gosselin F, Shea P D and Davies I W 2006 J. Org. Chem. 71 9548

  6. (a) Chaudhari P S, Pathare S P and Akamanchi K G 2012 J. Org. Chem. 77 3716; (b) Amir M and Kumar S 2004 Ind. J. Heterocycl. Chem. 14 51

  7. (a) Gavrilyuk J I, Lough A J and Batey R A 2008 Tetrahedron Lett. 49 4746; (b) Rostom S A, Shalaby M A and Demellawy E M 2003 Eur. J. Med. Chem. 38 959; (c) Zhang X, Xiao Y and Qian X 2008 Angew. Chem.Intl. Ed. 47 8025

  8. (a) Kilburn J P, Lau J and Jones, R C F 2001 Tetrahedron Lett. 42 2583; (b) Severinsen R, Kilburn J P and Lau J F 2005 Tetrahedron 61 5565

  9. (a) Sharma S, Srivastava V K and Kumar A 2002 Eur. J. Med. Chem. 37 689. (b) Hamad A S S and Hashem A 2002 J. Heterocycl. Chem. 39 1325

  10. (a) Appel R, Kleinstuck R and Ziehn K D 1971 Chem. Ber. 104 1335; (b) Dumciute J, Martynaitis V, Holzer W, Manelinckx S, Kimpe N D and Sackus A S 2006 Tetrahedron 62 3309

  11. Brain C T, Paul J M, Loong Y and Oakley P J 1999 Tetrahedron Lett. 40 3275

  12. Baxendale I R, Ley S V and Martinelli M M 2005 Tetrahedron 61 5323

  13. Levins C G and Wan Z K 2008 Org. Lett. 10 1755

  14. Maghari S, Ramezanpour S, Darviche F, Balalaie S, Rominger F and Bijanzadeh H R 2013 Tetrahedron 69 2075

  15. Xie Y, Liu J, Yang P, Shi X and Li J 2011 Tetrahedron 67 5369

  16. (a) Esher R and Buning P 1986 Angew. Chem. Int. Ed. Engl. 25 277; (b) Klose J, Bienert M, Mollenkop, C, Wehle D, Zhang, C -W, Carpino L A and Henklein P 1999 Chem. Commun. 1847

  17. (a) Desroses M, Wieckowski M and Odell L R 2011 Tetrahedron Lett. 52 4417; (b) Augustine J K, Bombrun A and Venkatachaliah S 2011 Tetrahedron Lett. 52 6814; (c) Wen X, Bakali J E, Deprez-Poulain R and Deprez B 2012 Tetrahedron Lett. 53 2440; (d) Poojari S P, Naik P and Krishnamurthy G 2012 Tetrahedron Lett. 53 4639; (e) Augustine J K, Vairaperumal V, Narasimhan S, Alagarsamy P and Radhakrishnan A 2009 Tetrahedron 65 9989

  18. (a) Meudt A, Scherer S and Nerdinger S WO 2005070879; (b) Hermann S DE 10063493 (2002); (c) Augustine J K, Bombrun A, Ramappa B and Boodappa C 2012 Tetrahedron Lett. 53 4422

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Acknowledgements

SS & SU are thankful to Dr. G.Manickam for his valuable advice and Syngene International Ltd. for providing facilities to carry out the research work.

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Authors and Affiliations

  1. School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India

    ANDIVELU ILANGOVAN & SHANMUGASUNDAR SARAVANAKUMAR

  2. Syngene International Ltd., Bangalore, 560 099, India

    SHANMUGASUNDAR SARAVANAKUMAR & SIDDAPPA UMESH

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  1. ANDIVELU ILANGOVAN
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  2. SHANMUGASUNDAR SARAVANAKUMAR
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  3. SIDDAPPA UMESH
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Correspondence to ANDIVELU ILANGOVAN.

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Supplementary Information

All additional information pertaining to characterization of all new compounds are given the supplementary information along with copies of 1H and 13C spectra and are available at www.ias.ac.in/chemsci.

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ILANGOVAN, A., SARAVANAKUMAR, S. & UMESH, S. T3P as an efficient cyclodehydration reagent for the one-pot synthesis of 2-amino-1,3,4-oxadiazoles. J Chem Sci 127, 797–801 (2015). https://doi.org/10.1007/s12039-015-0834-x

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  • DOI: https://doi.org/10.1007/s12039-015-0834-x

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