An effective and general method for the highly regioselective synthesis of 1-phenylpyrazoles from beta-enaminoketoesters, tandem Blaise-acylation adducts.
An effective and general route for the regioselective synthesis of 1-phenylpyrazoles has been developed from beta-enaminoketoesters prepared by tandem Blaise-acylation. This method is applicable to a very broad range of substrates, generating a diverse set of 3-aryl-5-alkyl, 3-alkyl-5-aryl, 3,5-diaryl, and 3,5-dialkyl substituted pyrazoles regioselectively. The dichotomous regioselective synthesis of isotopically discriminated 3-CD(3)-5-CH(3) and 3-CH(3)-5-CD(3) substituted pyrazoles showcases the power of this protocol.
Ko
Young Ok
YO
Department of Chemistry and Nano Science (BK21), Ewha Womans University, Seoul 120-750, Korea.
Chun
Yu Sung
YS
Park
Cho-Long
CL
Kim
Youngmee
Y
Shin
Hyunik
H
Ahn
Sungho
S
Hong
Jongki
J
Lee
Sang-gi
SG
D000215:Acylation; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D007659:Ketones; D009570:Nitriles; D011720:Pyrazoles