Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines

Jesse Kidd; Kristen Maiden; Jeremy B Morgan

doi:10.1016/j.tet.2016.03.031

Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines

Tetrahedron. 2016 Jun 30;72(26):3802-3807. doi: 10.1016/j.tet.2016.03.031.

Authors

Jesse Kidd¹, Kristen Maiden¹, Jeremy B Morgan¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403, USA.

Abstract

Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

Keywords: Aziridine; Indole; Regioselective; Ring opening; Tryptamine.

Grants and funding

R15 GM114766/GM/NIGMS NIH HHS/United States