An alternative highly regioselective synthetic method for the preparation of 3,5-disubstituted 4-formyl-N-arylpyrazoles in a one-pot procedure is reported. The methodology developed was based on the regiochemical control of the cyclocondensation reaction of β-enamino diketones with arylhydrazines. Structural modifications in the β-enamino diketone system allied to the Lewis acid carbonyl activator BF were strategically employed for this control. Also a one-pot method for the preparation of 3,5-disubstituted 4-hydroxymethyl-N-arylpyrazole derivatives from the β-enamino diketone and arylhydrazine substrates is described.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.7b02361DOI Listing

Publication Analysis

Top Keywords

method preparation
8
preparation 35-disubstituted
8
β-enamino diketone
8
unconventional method
4
method synthesis
4
synthesis 3-carboxyethyl-4-formylhydroxy-5-aryl-n-arylpyrazoles
4
3-carboxyethyl-4-formylhydroxy-5-aryl-n-arylpyrazoles alternative
4
alternative highly
4
highly regioselective
4
regioselective synthetic
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!