Title of article :
Parallel solution phase synthesis of a library of amino acid derived 2-arylamino-[1,3,4]-oxadiazoles
Author/Authors :
Gavrilyuk، نويسنده , , Julia I. and Lough، نويسنده , , Alan J. and Batey، نويسنده , , Robert A.، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2008
Pages :
4
From page :
4746
To page :
4749
Abstract :
A mild method for the synthesis of peptidomimetic 2-arylamino 5-substituted 1,3,4-oxadiazoles from Boc-protected α-amino acid derived hydrazides has been developed, and applied in a parallel solution-phase synthesis. The optimized reaction conditions involve a one-pot reaction of Boc-protected amino acid hydrazides with arylisothiocyanates in the presence of either Hg(II) chloride, Mukaiyama’s reagent (2-chloro-N-methylpyridinium iodide) or polymer supported Mukaiyama’s reagent, with triethylamine in dichloromethane at ambient temperature. The 1,3,4-oxadiazole products were obtained in good to excellent yields without any detectable epimerization. The reactions proceed via initial formation of thiosemicarbazides, followed by dehydrothiolative cyclization to the 1,3,4-oxadiazoles.
Journal title :
Tetrahedron Letters
Serial Year :
2008
Journal title :
Tetrahedron Letters
Record number :
1860458
Link To Document :
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