Recyclization of 2‐Aminobenzylimines and Thioaroylhydrazones of N‐Substituted N‐Hydroxy‐3‐oxobutanamides.

Abstract

2002 ring closure reactions ring closure reactions O 0130 -039Recyclization of 2-Aminobenzylimines and Thioaroylhydrazones of N-Substituted N-Hydroxy-3-oxobutanamides.-Based on a general scheme, a method of recyclizations is achieved by substituting amino groups of substituted amines and hydrazines to the exocyclic hydroxyl group in exo-trig-tautomeric ring-chain systems, thereby introducing another cyclic endotrig-structure in the end product. To test this idea, the condensation products of isoxazolidinones (I) with thioaroylhydrazines (II) and aminomethylaniline (IV) are examined. In the case of products (III), only one cyclic tautomer is observed, whereas products (V) and (VI) exhibit up to three accessible forms (e.g. (V), (VII), and (VIII)) in equilibrium, their ratio dependent on the nature of the solvent used. -(ZELENIN, KIRILL N.; LAGODA, IGOR V.; ALEKSEYEV, VALERIY V.; SINKKONEN, JARI; SHAIKHUTDINOV, ROUSTEM A.; PIHLAJA, KALEVI;