Diversity oriented heterocyclizations of pyruvic acids,aldehydes and 5-amino-<Emphasis Type="Italic">N</Emphasis>-aryl-1<Emphasis Type="Italic">H</Emphasis>-pyrazole-4-carboxamides: catalytic and temperature control of chemoselectivity |
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Authors: | Yana I Sakhno Svetlana V Shishkina Oleg V Shishkin Vladimir I Musatov Elena V Vashchenko Sergey M Desenko and Valentin A Chebanov |
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Institution: | (1) Division of Functional Materials Chemistry, State Scientific Institution, Institute for Single Crystal NAS of Ukraine, Lenin Ave. 60, Kharkiv, 61001, Ukraine; |
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Abstract: | 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-dihydropyrazolo1,5-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-tetrahydropyrazolo1,5-a]pyrimidine-7-carboxylic acids or 3-hydroxy-1-(1H-pyrazol-5-yl)-1,5-dihydro-2H-pyrrol-2-ones, respectively. |
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