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.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Carbohydrate Chemistry and Synthesis
Microwave-Assisted Synthesis and Applications
Publication details
- Journal / source
- Molecules
- Publisher
- MDPI AG
- Volume
- 31
- Issue
- 1
- Pages
- 164–164
- Publication date
- 1 January 2026
- Language
- EN