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À propos de : Preparation of α-(2,2-Diphenylhydrazino)lactones and RelatedCompounds by Radical Cyclization: Use of Glyoxylic AcidHydrazone Derivatives        

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  • Preparation of α-(2,2-Diphenylhydrazino)lactones and RelatedCompounds by Radical Cyclization: Use of Glyoxylic AcidHydrazone Derivatives
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  • Glyoxylic acid diphenylhydrazone (2a) and the corresponding O-benzyloxime (2b) are easily esterifiedin high yield by β-bromo alcohols. The resulting esters undergo radical cyclization to α-(2,2-diphenylhydrazino)- or α-[(phenylmethoxy)amino]lactones on treatment with tributyltin hydride.Esters for radical cyclization were also made using a β-(phenylseleno) alcohol and an enol ether.Several derivatives of glyoxylic acid were evaluated, but none was as effective as 2a or 2b. Theimine 28 was prepared by an indirect route; it undergoes radical cyclization with displacement ofthe nitrogen substituent (28 → 30) so that an α-amino lactone can be generated by acid hydrolysisof the cyclization product.
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