Serendipitous Discovery of a New Method for the Catalytic Synthesis of Indole-fused Benzazepanes

Authors

Edward Gluzman, DePaul Department of ChemistryFollow
Paul A. Vadola, DePaul UniversityFollow

Faculty Advisor

Dr. Paul Vadola

Abstract

We report here on our investigations into the application of 1,5-hydride transfer cyclization mechanisms to the synthesis of 2,3-disubstituted benzofurans and indoles. We found that PtI₄ in MeCN at 120 ºC was indeed capable of activating the alkyne, however, the expected 2,3-disubstituted indole product was not observed. Instead we isolated an indolyl-3-benzazepane via an unexpected intramolecular Steven’s rearrangement/ring expansion. While this transformation has been previously reported our method may prove to have increased substrate scope and more practical reaction conditions. Further studies are underway to optimize the reaction conditions and to fully explore the scope and mechanism of the transformation.

Recommended Citation

Gluzman, Edward and Vadola, Paul A. (2016) "Serendipitous Discovery of a New Method for the Catalytic Synthesis of Indole-fused Benzazepanes," DePaul Discoveries: Volume 5, Article 4.
Available at: https://via.library.depaul.edu/depaul-disc/vol5/iss1/4