Access to fused π-extended acridone derivatives through a regioselective oxidative demethylation. Issue 32 (4th August 2021)

• Record Type: Journal Article
• Authors: Ding, Weiwei; Zhang, Gang
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 32(2021)
• Page Start: 6985
• Page End: 6989
• Publication Date: 2021-08-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01249e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The oxidative demethylation of dimethoxyacridone with ceric ammonium nitrate gives an ortho -quinone regioselectively, which was used to synthesize π-extended acridone derivatives. 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.