A. Borah, P. Phukan
Dec 24, 2013
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Journal
Journal of Chemical Sciences
Abstract
Abstract1,3-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. Graphical Abstract4,6-Disubstituted-1,3-oxazinan-2-one analogues were synthesized from corresponding homoallylic carbamates. Sharpless dihydroxylation (racemic) of the homoallylic carbamate followed by NaH-assisted cyclization produced 6-(hydroxymethyl)-1,3-oxazinan-2-one in high yield.