Chemoselective Aza-Michael Addition of Enolizable Heterocyclic Imine-Thiols to Levoglucosenone.

ABSTRACT: Heterocyclic sulfur and nitrogen containing compounds capable of forming an equilibrium: thiol/imine = thione/amine (N=C-S-H ⇌ H-N-C=S) were reacted with levoglucosenone (LG) in the presence of triethylamine. Unexpectedly, the only isolated products were the result of the aza-Michael addition. No S-adducts were detected. All products were crystalline with good to excellent yields. The structure of products was determined using NMR, MS, and single-crystal X-ray analysis.

SUBMITTER: Mauger A 

PROVIDER: S-EPMC12787532 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature