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Recyclizations of 2‐aminobenzylimines and thioaroylhydrazones of N ‐substituted N ‐hydroxy‐3‐oxobutanamides
Author(s) -
Zelenin Kirill N.,
Lagoda Igor V.,
Alekseyev Valeriy V.,
Sinkkonen Jari,
Pihlaja Kalevi,
Shaikhutdinov Roustem A.
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390428
Subject(s) - chemistry , tautomer , ring (chemistry) , solvent , condensation , molecule , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , physics , thermodynamics
A universal scheme is proposed for the molecular design of heterocyclic recyclizations by replacing the exocyclic hydroxyl groups in exo‐trig ‐ ring‐chain tautomeric molecules with substituted amines or hydrazines. The practical applicability of this approach is demonstrated by the condensations of 5‐hydroxy‐5‐methyl‐3‐isoxazolidinones with thioaroyl‐hydrazines and 2‐aminomethylaniline. The condensation products were studied by modern 1 H, 13 C and 15 N NMR spectroscopic methods using three solvents: CDC1 3 , DMSO[D 6 ] and CD 3 CN. The solvent was found to have a strong effect to the relative amounts of the tautomers.