Abstract
Regioselective and stereoselective methods were developed for the synthesis of 4-aryl-2-oxo-3-(1-pyridinio)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridin-6-olates from pyridinium ylides and α,Β-unsaturated nitriles. The compounds were also obtained by the condensation of aromatic aldehydes, cyanoacetamide, and pyridinium ylides. It was established that these reactions take place through the corresponding Michael adducts, which undergo heterocyclization in the form of the anti conformers to substituted 3,4-trans-1,2,3,4-tetrahydropyridin-6-olates.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 363–369, March, 1990.
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Shestopalov, A.M., Sharanin, Y.A. & Litvinov, V.P. Stereochemistry of the reaction of pyridinium ylides with α,Β-unsaturated nitriles. Chem Heterocycl Compd 26, 311–317 (1990). https://doi.org/10.1007/BF00472552
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DOI: https://doi.org/10.1007/BF00472552