Iodine-Mediated C?C Double Bond Cleavage toward Pyrido[2,1-b]quinazolinones

A transition-metal-free C???C double bond cleavage reaction employing molecular iodine is described. In the presence of K2CO3 as the base, I2-mediated C???C bond cleavage followed by intramolecular annulation of N-(2-vinylaryl)pyridin-2-amine substrates produces pyrido- [2,1-b]quinazolinones and related heterocyclic compounds. This reaction can be completed on a gram scale and has been successfully applied to the synthesis of compounds with important biological properties, including efflux pump inhibitory and antiallergic activities.

Automated summary

This study describes a transition-metal-free C???C double bond cleavage reaction using molecular iodine as the catalyst. In the presence of K2CO3, the I2-mediated C???C bond cleavage followed by intramolecular annulation reaction can generate pyrido-[2,1-b]quinazolinones and related heterocyclic compounds with important biological activities.