Abstract
Polycyclic heteroarenes are important scaffolds in the construction of pharmaceuticals. We have previously developed a series of novel heterocyclic iodoniums. In our current work, these unique iodoniums were employed to construct various complex polycyclic heteroarenes with structural diversity via tandem dual arylations. As a result, indole, thiophene and triphenylene motifs were fused into these heterocycles with high molecular quality, which might provide promising fragments in drug discovery. Moreover, these heterocycles could be diversified at a late stage.
Highlights
Polycyclic heteroarenes are important scaffolds in the construction of pharmaceuticals.1 Compared with polycyclic aromatic hydrocarbons, heterocycles exhibit improved solubility and bioavailability, which make them promising drug candidates.2 Many heterocycles are reported as kinase inhibitors, anti-infective and antibacterial agents (Fig. 1)
We have developed a series of new Heterocyclic iodoniums (HCIs),10 and we wish to fully investigate their synthetic application potentials to obtain diverse heterocycles via tandem transformations
We thoroughly investigated tandem dual aminations of HCIs with various amines to produce indole-fused polycyclic scaffolds
Summary
Polycyclic heteroarenes are important scaffolds in the construction of pharmaceuticals.1 Compared with polycyclic aromatic hydrocarbons, heterocycles exhibit improved solubility and bioavailability, which make them promising drug candidates.2 Many heterocycles are reported as kinase inhibitors, anti-infective and antibacterial agents (Fig. 1). Using our recently discovered odor-free triethylammonium N-benzyldithiocarbamate (M1) as the sulfur source donor,8a reactions of HCIs and M1 under mediation of copper sulfate could smoothly furnish benzothiophene-fused heterocyclic frameworks, including chromone (5a), quinoline (5b), isoquinoline (5c) and coumarin (5d), as shown in Scheme 4.
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