1-(Cyanoacetyl)-3,5-dimethylpyrazole as Active Methylene Compound in Hantzsch-type Pyridine Synthesis: A Convenient and Highly Effective Approach to 3,5-Dicyano-4-(het)aryl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates |
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| Authors: | Victor V Dotsenko Sergey G Krivokolysko Victor P Litvinov |
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| Institution: | (1) “ChemEx” Laboratory, Vladimir Dal‘ East Ukrainian National University, Lugansk, Ukraine;(2) Russian Academy of Sciences, Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation |
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| Abstract: | Summary. Reaction of 1-(cyanoacetyl)-3,5-dimethylpyrazole with (E)-2-cyano-3-(het)arylprop-2-enethioamides was used for the synthesis of N-methylmorpholinium 3,5-dicyano-4-(het)aryl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates for the first time. The latter were
also obtained in a multicomponent one-pot mode via the condensation of cyanothioacetamide with corresponding aldehydes and above 1-cyanoacetylpyrazole in the presence of N-methylmorpholine under mild conditions. Thiolates 1 exist as a pair of cis/trans-diastereomers in different ratios (from 3:4 to 2:1).
Last author was Deceased on February 26, 2007 |
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| Keywords: | , Heterocycles, Cyclizations, Michael addition, Pyridine-2-thiolates, Cyanoacetylpyrazole, |
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