Vereshchagin, Anatoly N.; Iliyasov, Taygib M.; Karpenko, Kirill A.; Smirnov, Vladimir A.; Ushakov, Ivan E.; Elinson, Michail N. published the artcile< Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines>, Electric Literature of 94-02-0, the main research area is tetrahydropyridine preparation diastereoselective; benzylidenemalononitrile oxocarboxylic acid aromatic aldehyde multicomponent heterocyclization ammonium acetate.
A novel four-component diastereoselective synthesis of polysubstituted tetrahydropyridines (4SR,6RS)-I (R = H, 3-F, 4-Me, 4-Cl, etc.; R1 = Me, Et, Ph, 4-bromophenyl; R2 = Me, Et) is reported. The Michael addition – Mannich reaction – cyclization – dehydration cascade of benzylidenemalononitriles RC6H4CH=C(CN)2, esters of 3-oxocarboxylic acids R1C(O)CH2C(O)OR2, aromatic aldehydes RC6H4CHO, and ammonium acetate in methanol provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine- 3-carboxylates (4SR,6RS)-I with two stereocenters in 66-92% yields. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays dual role acting as a base and as a nitrogen source. The formation of single diastereomer was confirmed by singe crystal X-ray diffraction studies.
Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Electric Literature of 94-02-0.
Referemce:
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