An Operationally Simple Approach to Indole Derivatives from 2-Alkenylanilines Utilizing an Oxidation-Intramolecular Cyclization-Elimination Sequence

Lauren N Hines; Jacob R King; Alex C Atwood; Rachel M Chapman; Matthew B Griffey; Christine R Tutwiler; Christopher Jon Monceaux

doi:10.3390/molecules28247968

An Operationally Simple Approach to Indole Derivatives from 2-Alkenylanilines Utilizing an Oxidation-Intramolecular Cyclization-Elimination Sequence

Molecules. 2023 Dec 6;28(24):7968. doi: 10.3390/molecules28247968.

Authors

Lauren N Hines¹, Jacob R King¹, Alex C Atwood¹, Rachel M Chapman¹, Matthew B Griffey¹, Christine R Tutwiler¹, Christopher Jon Monceaux¹

Affiliation

¹ Department of Chemistry, Radford University, Radford, VA 24142, USA.

Abstract

Herein we describe a novel route to indole derivatives from a variety of N-substituted 2-alkenylanilines. This route features three operationally simple steps: (1) oxidation to convert N-substituted 2-alkenylanilines into epoxide intermediates, (2) intramolecular cyclization, and (3) the acid-catalyzed elimination of water.

Keywords: epoxidation; intramolecular cyclization; metal-free indole synthesis.

Grants and funding

The authors would like to thank Radford University and the Office of Undergraduate Research and Scholarship (OURS) for their funding for this research.