Tandem CuAAC/Ring Cleavage/[4 + 2] Annulation Reaction to Synthesize Dihydrooxazines and Conversion to 2-Aminopyrimidines
Weiguang Yang, Yu Zhao, Qingxia Bu, Li Li, Baojing Zhou, Zunnan Huang
Abstract
A tandem CuAAC/ring cleavage/[4 + 2] annulation reaction of terminal ynones, sulfonyl azides, and oximes has been developed to synthesize functionalized dihydrooxazines under mild conditions. In particular, intermediate N-sulfonyl acylketenimines are the first example of a 4π-system participating in [4 + 2] cycloadditions, and dihydrooxazines can convert to 2-aminopyridines through ring cleavage under basic conditions.
Topics & Concepts
AnnulationChemistryCleavage (geology)TandemSulfonylRing (chemistry)Combinatorial chemistryStereochemistryOrganic chemistryCatalysisEngineeringComposite materialMaterials scienceAlkylGeotechnical engineeringFracture (geology)Synthesis and Catalytic ReactionsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms