Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones

• Main Authors: Marković Rade, Rašović Aleksandar S., Baranac Marija M., Stojanović Milovan, Steel Peter, Jovetić Stanka L.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2004-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: thiazolidine; enaminone; lawesson’s reagent; 1,2-dithiole; 3; 3aλ4,4-trithia
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390411909M.pdf

The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.