Iodine-Promoted Oxidative Cyclization of Acylated and Alkylated Derivatives from Epoxides toward the Synthesis of Aza Heterocycles
Alageswaran Jayaram, Karthick Govindan, Vijaya Raghavan Kannan, Vijay Thavasianandam Seenivasan, Nian‐Qi Chen, Wei‐Yu Lin
Abstract
A new method for directly synthesizing acylated and alkylated quinazoline derivatives by the epoxide ring-opening reaction in the presence of I 2 /DMSO with 2-aminobenzamide is described herein. The developed mild protocol is efficient and displays a wide variety of functional group tolerance and substrate-controlled high selectivity, and the application of a continuous flow technique allows for faster reaction time and higher yields. Moreover, the robustness of the method is applicable in gram-scale synthesis.
Topics & Concepts
AlkylationChemistryEpoxideCombinatorial chemistryFunctional groupIodineQuinazolineNucleophileOrganic chemistryCatalysisPolymerQuinazolinone synthesis and applicationsAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization Methods