DEAE-cellulose-catalyzed synthesis of 5-hydroxy-isoxazolidines and their synthetic uses towards nucleoside analogues

Abstract

5-Hydroxy-isoxazolidinic heterocycles can be easily prepared from hydroxamic acids and suitable ,unsaturated aldehydes or ketones in good yields from solid state synthesis, selectively promoted by DEAE-C. The synthesized products were efficiently derivatized with representative heterobases for the preparation of nucleoside analogues suitable for biological evaluation and SAR analysis.

Diethylaminoethyl cellulose (DEAE-C) between chromatography and synthetic applications

“…The synthesized products were efficiently derivatized with representative heterobases for the preparation of nucleoside analogues with a methylene group in the position 3 of heterocyclic ring and e benzoyl group at the nitrogen atom, suitable for biological evaluation and SAR analysis (see Scheme 9). 66 Our interest in these and other methodologies is actively pursued and hopefully further investigation could offer new pathway to isoxazolidines and other applications of DEAE-C catalysis in organic chemistry.…”

A Simple Environmentally Friendly Method for the Synthesis of Hydroxyisoxazolidine Derivatives

“…[1,5,[7][8][9] For the last fifty years, there have been few articles about the synthesis of hydroxyl isoxazolidines from unsaturated carbonyl compounds and hydroxylamine (or its derivatives/ analogs). [4,5,[17][18][19][20][21][22][23][24][25][26][27][28][29] The formation of 5-hydroxyisoxazolidines easily occurred in neutral pH at room temperature (in rather an anhydrous condition), few examples of 3-hydroxyisoxazolidines synthesis are also known, but only for benzohydroxyamic acid and its analogs (p-NO 2 , p-Br and 2,3,5-(CH 3 ) 3 ). Hydroxy isoxazolidines are rather unstable (decompose when exposed to light and upon heating) and undergo chain-ring tautomerism.…”