A Novel Access to 2-Aminofuranones via Cyclization of Functionalized γ-Hydroxy-α,β-butenoates Derived fromN-Hydroxybenzotriazole Esters of α-Hydroxy Acids

Abstract

The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of g-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by Nhydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.

Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers

“…We synthesized PhDL from commercially available compound 1 (R 1 ¼ Ph in Scheme 3) by referring to the synthesis of a similar compound. 33,34 The compound 1 (1 equiv.) was reacted with acetyl chloride (2.8 equiv.)…”