Artem Kireev - One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols

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  Publication Details (including relevant citation   information):

  J. Org. Chem. 2007, 72, 3443


  Heterocyclic privileged medicinal scaffolds involving pyridine,   1,4-dihydropyridine, chromeno[2,3-b]pyridine,  and   dihydro-1,4-dithiepine frameworks are prepared via a   single-step  multicomponent reaction of structurally diverse   aldehydes with various  thiols and malononitrile.   Mechanistic studies of the synthetic pathway  leading to   pyridines reveal that 1,4-dihydropyridines undergo   oxidation  by the intermediate Knoevenagel adducts rather   than by air oxygen. The  use of   o,o‘-disubstituted aromatic aldehydes leads to   the  corresponding 1,4-dihydropyridines, whereas salicylic   aldehydes result  in chromeno[2,3-b]pyridines.   Reactions of ethanedithiol as a  thiol component produce   dimeric pyridines with sterically unencumbered  aldehydes,   while o,o‘-disubstituted aromatic   aldehydes  give dihydro-1,4-dithiepines. Thus, depending on   the aldehyde and thiol  types, diverse libraries of   medicinally relevant compounds can be  prepared by a simple   one-step process involving no chromatography.

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