Oxidative difunctionalization of 2-amino-4H-pyrans in iodobenzene diacetate and N-chlorosuccinimide: reactivity, mechanistic insights, and DFT calculations.

Santhosh Reddy Mandha, Manjula Alla, Vittal Rao Bommena, Jagadeesh Babu Nanubolu, Santosh Kumar Lingala, Soujanya Yarasi

Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.

The Journal of organic chemistry 2012 Dec 7

filter terms:

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).

Citation

Santhosh Reddy Mandha, Manjula Alla, Vittal Rao Bommena, Jagadeesh Babu Nanubolu, Santosh Kumar Lingala, Soujanya Yarasi. Oxidative difunctionalization of 2-amino-4H-pyrans in iodobenzene diacetate and N-chlorosuccinimide: reactivity, mechanistic insights, and DFT calculations. The Journal of organic chemistry. 2012 Dec 7;77(23):10648-54