Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

With triethylamine as a vinylene source, a convenient protocol for the regioselective synthesis of beta,gamma-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups to be concurrently installed into the pyridine rings. This process demonstrates a new conversion pathway for the simultaneous dual C(sp(3))-H bond functionalization of tertiary amines, wherein the transient acyclic enamines generated in situ undergo the Povarov reaction.

Automated summary

By using triethylamine as a vinylene source, a convenient protocol for the regioselective synthesis of beta,gamma-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been developed. The deaminative cyclization can also be extended to long-chain tertiary alkylamines, allowing diverse alkyl groups to be simultaneously introduced into the pyridine rings. This process demonstrates a new conversion pathway for simultaneous dual C(sp(3))-H bond functionalization of tertiary amines, in which the transient acyclic enamines generated in situ undergo the Povarov reaction.