Activation of the NC-H bond of Baylis-Hillman adducts of N-methylisatin with CAN/ROH

Abstract

A facile method for activation of the NC-H bond of N-methylisatin and Baylis-Hillman adducts of N-methylisatin with cerium ammonium nitrate (CAN) and saturated and unsaturated alcohols is reported. Adducts bearing an ester group at the activated alkene afford functionalized ethers, while those with a nitrile afforded ethers and nitrated aromatic products in good yield. © 2006 Elsevier Ltd. All rights reserved.