Abstract:
The Knövenagel–Michael–Mannich cascade reaction of aromatic aldehyde (3 equiv.), malononitrile (2 equiv.) and ammonium acetate or aqueous ammonia provides convenient stereoselective access to cis,cis-2,4,6-triaryl-3,3,5,5-tetracyanopiperidines in 62–94% yields. Six new bonds form as a result of the domino process, ammonium acetate serving as a nitrogen source.
Citation:
A. N. Vereshchagin, K. A. Karpenko, M. N. Elinson, E. O. Dorofeeva, A. S. Goloveshkin, M. P. Egorov, “Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines”, Mendeleev Commun., 28:4 (2018), 384–386
Linking options:
https://www.mathnet.ru/eng/mendc1774
https://www.mathnet.ru/eng/mendc/v28/i4/p384
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Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Alexander S. Goloveshkin, Mikhail P. Egorov, “Stereoselective domino assembling of five molecules: one-pot approach to (2 ′ R * ,3S * ,4 ′ R * )-2 ′ ,4 ′ -diaryl-1 ′ ,4 ′ -dihydro-2 ′ H-spiro[indoline-3,3 ′ -pyridines]”, Comptes Rendus. Chimie, 23:2 (2020), 159
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M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, N. A. Leonova, M. P. Egorov, “On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N'-dimethylbarbituric acid and cyclohexane-1,3-diones”, Mendeleev Commun., 30:1 (2020), 15–17
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A. N. Vereshchagin, K. A. Karpenko, T. M. Iliyasov, M. N. Elinson, E. O. Dorofeeva, A. N. Fakhrutdinov, M. P. Egorov, “Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates”, Russ Chem Bull, 67:11 (2018), 2049
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