INVESTIGATION OF THE REACTIVITIES AND TAUTOMERISM OF AZOLIDINES. 46. PMR SPECTRA AND STRUCTURES OF THE PRODUCTS OF HYDROXYMETHYLATION AND AMINOMETHYLATION OF 2-IMINO-5-ARYLIDENE-4-THIAZOLIDINONES

Article abstract of DOI:10.1007/BF00506099

On the basis of dual reactivity concepts, it is shown that the hydroxy- and aminomethylation of ambifunctional 2-imino-5-R-benzylidene-4-thiazolidinones (R = H, p-Cl, p-OCH3, p-Br, and p-F) should be directed to the same reaction center.On the basis of PMR spectroscopic data, it was confirmed that this center is the exocyclic nitrogen atom.It was established that 2-piperidinomethylamino-5-R-benzylidene-4-thiazolinones (R = H, p-Cl, p-NO2, p-OCH3, p-Br, and p-F) exist in d₆-DMSO primarily in the form of E conformers of the amino form.The E conformers of the latter compounds are chelate structures with an intramolecular hydrogen bond.