Angewandte Chemie · 2014 · 53 citations · 59 references
Natural SciencesChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAnnulation ReactionsAzepine ChemistryIndole SynthesisMedicinal Chemistry ApplicationsMild Reaction ConditionsTriazole ChemistryTriazole Synthesis
Abstract A convenient and efficient synthetic method has been developed to construct highly functionalized N‐bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular CH functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity. Several interesting derivatizations of the resulting products demonstrate that this method is synthetically valuable and useful.
59
Huw M. L. Davies, Paul R. Bruzinski, Debra H. Lake et al. · Journal of the American Chemical Society · 1996 · 466 citations