Oxidative difunctionalization of 2-amino-4H-pyrans was accomplished with iodobenzene diacetate (IBD) and N-chlorosuccinimide (NCS) reagents in alcoholic medium. 2-Amino-4H-pyrans undergo geminal dialkoxylation with the migration of an amino group (1a,b, 2a-i, 3a,b, and 4) in IBD, whereas with NCS addition of both chlorine and alkoxy groups takes place across the chromene double bond (6a-i).
An operationally simple and efficient protocol for the construction of dihydrofuran derivatives has been accomplished via a sequential addition of N-chlorosuccinimide and a base to 2-amino-4H-pyran derivatives in alcohol medium. The one-pot protocol proceeding via tandem oxidative difunctionalization and ring contraction provides an entirely new strategy for the construction of the dihydrofuran skeleton.
Increasing environmental awareness and economic concerns have led to the consideration of highly efficient one-pot, three-component, green approaches for important organic synthons. We describe here a simple, elegant and high yielding protocol for the synthesis of α-aminophosphonates in totally solvent-free, catalyst-free conditions by reacting aldehydes, amines and trimethyl phosphite at ambient temperature.
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