P. Dragovich, Thomas M. Bertolini, B. Ayida
Jan 29, 2007
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron
Abstract
Abstract A general procedure is described for the regiospecific preparation of 1-substituted-5-hydroxy-1H-pyrazoles containing differentiated ester moieties at the 3- and 4-positions. This process involves the coupling of monosubstituted benzyl carbazates with various malonyl chlorides or acids, deprotection of the coupling products via catalytic hydrogenation, and subsequent derivatization of the resulting hydrazides with monoalkyl oxalyl chlorides. The 5-hydroxy-1H-pyrazoles are readily transformed to the corresponding trifluoromethane sulfonates, which undergo palladium-mediated Suzuki coupling with a variety of boronic acids (aryl, heteroaryl, and alkenyl) in moderate to excellent yields (24–92%). The ester groups present in one of the resulting 1,5-disubstituted-1H-pyrazoles are further modified by selective hydrolysis or conversion to the corresponding dicarboxylic acid derivative followed by selective mono-esterification.