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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Access to fused π-extended acridone derivatives through a regioselective oxidative demethylation
1Jiangsu Co-Innovation Center for Efficient Processing and Utilization of Forest Products, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. China. gangzhang@njfu.edu.cn.
Abstract:
The oxidative demethylation of ortho-dimethoxyacridone with ceric ammonium nitrate (CAN) regioselectively furnished an ortho-quinone leaving a methoxyl group unreacted, which further condensed with aromatic ortho-diamines to afford angularly fused π-extended acridone derivatives. Crystallographic analysis reveals the distinct manner of molecular packing in the crystals according to the dimension of π-extension. The benzene at the turning point possesses a shorter outer bond and a longer inner bond, which affects molecular conjugation and results in weakened aromaticity.
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