ChemInform Abstract: Oxidative Difunctionalization of 2‐Amino‐4H‐pyrans in Iodobenzene Diacetate and N‐Chlorosuccinimide: Reactivity, Mechanistic Insights, and DFT Calculations.

Abstract

Oxidative Difunctionalization of 2-Amino-4H-pyrans in Iodobenzene Diacetate and N-Chlorosuccinimide: Reactivity, Mechanistic Insights, and DFT Calculations. -In the presence of PhI(O-Ac)2 and simple alcohols, 2-aminopyrans undergo unusual geminal dialkoxylation with 1,2-migration of the amino group. Reaction of (I) with NCS and alcohols leads to compounds of type (IV) by stepwise addition of chlorine and alkoxy groups. However, starting from the amine (V) the imine (VII) is obtained. The mechanism is discussed. -(MANDHA, S. R.; ALLA*, M.; BOMMENA, V. R.; NANUBOLU, J. B.; LINGALA, S. K.; YARASI, S.; J. Org. Chem. 77 (2012) 23, 10648-10654, http://dx.doi.org/10.1021/jo301801b ; CPC Div., Indian Inst. Chem. Technol., CSIR, Hyderabad 500 607, India; Eng.) -Jannicke 23-128