Diversity oriented heterocyclizations of pyruvic acids, aldehydes and 5-amino-N-aryl-1H-pyrazole-4-carboxamides: catalytic and temperature control of chemoselectivity.
Heterocyclization reactions of pyruvic acids, aromatic aldehydes and 5-amino-N-aryl-1H-pyrazole-4-carboxamides yielding four different types of final compounds are described. The reactions involving arylidenpyruvic acids lead with high degree of selectivity to either 4,7-dihydropyrazolo[1,5-a]pyrimidine-5-carboxylic acids or 5-[(2-oxo-2,5-dihydrofuran-3-yl)amino]-1H-pyrazoles, depending on the catalyst type or temperature regime. The interactions based on arylpyruvic acids can take place under kinetic or thermodynamic control producing 7-hydroxy-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-7-carboxylic acids or 3-hydroxy-1-(1H-pyrazol-5-yl)-1,5-dihydro-2H-pyrrol-2-ones, respectively.
Division of Functional Materials Chemistry, State Scientific Institution, Institute for Single Crystal NAS of Ukraine, Lenin Ave 60, Kharkiv 61001, Ukraine.
Yana I
YI
Sakhno
Svetlana V
SV
Shishkina
Oleg V
OV
Shishkin
Vladimir I
VI
Musatov
Elena V
EV
Vashchenko
Sergey M
SM
Desenko
Valentin A
VA
Chebanov
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D019289:Pyruvic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D014961:X-Ray Diffraction
D000447:Aldehydes; D006571:Heterocyclic Compounds; D011720:Pyrazoles; C031280:pyrazole; D019289:Pyruvic Acid