One-Pot Methylenation-Cyclization Employing Two Molecules of CO2 with Arylamines and Enaminones

J Org Chem. 2020 Jan 17;85(2):912-923. doi: 10.1021/acs.joc.9b02858. Epub 2019 Dec 18.

Abstract

One-pot methylenation-cyclization employing two molecules of CO2 with enaminones and primary aromatic amines was discussed for the first time to access cyclized products. This 1,5,7-triazabicyclo[4.4.0]dec-5-ene and ZnCl2-catalyzed procedure was characterized by the selective conversion of two molecules of CO2 into methylene groups in a multicomponent cyclization reaction. According to the computational study and control experiments, the reaction might proceed through the generation of bis(silyl)acetal and condensation of arylamine and aza-Diels-Alder processes. Moreover, the resulting products will probably be potential organic building blocks with adjustable photophysical properties.