Design and synthesis of two pyrazole libraries based on o-hydroxyacetophenones.
Two new solid-phase syntheses of substituted pyrazoles are described. The first includes supporting an o-hydroxyacetophenone on Merrifield resin, Vilsmeier-Haack formylation on the methyl group and cyclization with a substituted hydrazine to afford a pyrazole ring with two diversity centers. The second starts from o-hydroxyacetophenone supported on Wang resin, which undergoes a Claisen condensation with a carboxylic acid ester to yield a 1,3-dicarbonyl compound that cyclizes to a pyrazole using a hydrazine. Both methods have been used to synthesize two small pyrazole libraries.
Borrell
José I
JI
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, E-08017 Barcelona, Spain. j.i.borrell@iqs.url.edu
Schuler
Elisabeth
E
Teixidó
Jordi
J
Michelotti
Enrique L
EL
D000098:Acetophenones / Q000737:chemistry*; D000818:Animals; D001671:Biochemistry / Q000379:methods; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005659:Fungicides, Industrial / Q000737:chemistry / Q000494:pharmacology; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology; D011720:Pyrazoles / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000098:Acetophenones; D005659:Fungicides, Industrial; D006540:Herbicides; D007306:Insecticides; D011720:Pyrazoles; C087908:2'-hydroxyacetophenone