6533b7cffe1ef96bd12585ae

RESEARCH PRODUCT

One-Pot Oxidative C–H Activation/Aza-Prins-Type Reaction of Tertiary Alkynylamines: A Counter Ion-Induced Iminium Ion–Alkyne Cyclization

Stefan PuschLeander GeskeJulio Cesar Orejarena PachecoTill Opatz

subject

chemistry.chemical_classificationchemistry010405 organic chemistryOrganic ChemistryIminiumAlkyneOxidative phosphorylationCounterion010402 general chemistry01 natural sciencesMedicinal chemistry0104 chemical sciencesIon

description

Herein, the design and development of a new one-pot and metal-free oxidative C-H activation/aza-Prins type cyclization of alkynylamines is reported. The scope of this method was demonstrated by the preparation of ten new pyrido[2,1-a]isoquinolines in moderate to high yields (38-92%). Furthermore, a mechanistic proposal for the alkyne aza-Prins cyclization is described based on DFT calculations.

https://doi.org/10.1021/acs.joc.0c02737