USE OF THE α-AMINATION REACTION FOR THE SYNTHESIS OF PYRAZOLE DERIVATIVES CONTAINING CARBO- AND HETEROCYCLIC SUBSTITUENTS ON THE NITROGEN ATOM
DOI:
https://doi.org/10.1007/1259Keywords:
azodicarboxylate, cyclohexanone, cyclopentanone, N-substituted piperidones, pyrazoles, L-proline, tetrahydro-γ-pyranone, stereoselective α-aminationAbstract
A method has been developed for the synthesis of pyrazoles with carbo- and heterocyclic substituents on the nitrogen atom based on the α-amination reaction of carbo- and heterocyclic ketones, using azodicarboxylate–L-proline system with subsequent interaction with malonodialdehyde tetramethyl-acetal. In the case of carbocyclic ketones and tetrahydro-γ-pyranone, the reaction occurs stereo-selectively to give chiral hydrazines and pyrazoles. With derivatives of piperidin-4-one, α-amination is accompanied by racemization.
Authors: A. A. Utkina, A. V. Kurkin, and M. A. Yurovskaya.
English translation in Chemistry of Heterocyclic Compounds, 2012, 48 (2), pp 327-333
