beta-aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction

Citation
A. Alberola et al., beta-aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction, J CHEM S P1, (24), 1998, pp. 4061-4065
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
24
Year of publication
1998
Pages
4061 - 4065
Database
ISI
SICI code
0300-922X(199812):24<4061:BITRSO>2.0.ZU;2-5
Abstract
beta-Aminoenones react with monoalkyl hydrazines to give regioselectively 1 ,3,5-trisubstituted pyrazoles. The mechanism and level of regioselectivity depend on both the substitution pattern of the substrates and the reaction conditions. When the least bulky substituent is attached at the beta-positi on of the enone, a high regioselectivity is obtained, usually higher than t hat from equivalent beta-diketones. If the beta-substituent is the bulkiest group, the regioselectivity decreases. Nevertheless, in the conditions rep orted in this paper, it is possible to prepare pyrazoles not obtainable fro m beta-diketones.