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    • Synthesis of new 4,6-disubstituted-1,3-oxazinan-2-one analogues

      Arun Jyoti Borah Prodeep Phukan

      Regular Articles Volume 125 Issue 6 November 2013 pp 1503-1510

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/125/06/1503-1510

    • Keywords

       

      1,3-Oxazinan-2-one; homoallylic carbamates; Sharpless dihydroxylation; iodine; heterocyclic compound.

    • Abstract

       

      1,3-Oxazinan-2-one analogues are important heterocyclic compounds having significant biological activities. This study reports the synthesis of eight new 4,6-disubstituted -1,3-oxazinan-2-one analogues from corresponding homoallylic carbamates. Homoallylic carbamates were synthesized via a three-component reaction of aldehyde, allyltrimethylsilane and benzyl carbamate in presence of iodine as catalyst. In the next step, homoallylic carbamates were subjected to Sharpless dihydroxylation (racemic) to produce 3,4-dihydroxybutylcarbamate derivatives. This product was then treated with NaH in tetrahydrofuran (THF) to produce the desired 6-(hydroxymethyl)-1,3-oxazinan-2-one in high yield.

    • Author Affiliations

       

      Arun Jyoti Borah1 Prodeep Phukan1

      1. Department of Chemistry, Gauhati University, Guwahati 781 014, India

    • Dates

       
      Published
      November 2013
      Manuscript received
      2 August 2012
      Manuscript revised
      17 August 2013
      Accepted
      21 August 2013

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