Zn-Mediated Synthesis of 3-Substituted Indoles Using a Three-Component Reaction Approach

The synthesis of 3-substituted indoles was investigated through a multicomponent reaction approach by using aldehydes, indole and malononitrile as the reagents

Daniele Anselmo

2012

Scholarcy highlights

  • The synthesis of 3-substituted indoles was investigated through a multicomponent reaction approach by using aldehydes, indole and malononitrile as the reagents
  • The 3-CR was studied in detail that covered the influence of the base, solvent, reagent stoichiometry and involved stability studies
  • The results led to a mechanistic proposal in which the benzylidene malononitrile intermediate plays a central role; it is one of the major species that is formed in most of the catalytic reactions studied
  • It provided a prelude for the in situ reaction with the malononitrile reagent, which most probably affords a complex mixture of N-containing heterocycles
  • The reaction parameters were investigated and the selectivity for the 3-CR product was examined under various conditions
  • Selectivity for the target compound is significantly compromised by side-product formation due to in situ reaction of the intermediate species with malononitrile, which affords N-heterocyclic structures
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