Issue 7, 2015

A biomass-involved strategy for the synthesis of N-arylated dibenzo[b,e][1,4]oxazepin-11(5H)-ones, acridones, 7,12-dihydrodibenzo[b,e][1,4]oxazocin-6H-ones and dibenzo[b,f]azepin-10(11H)-ones

Abstract

An efficient method for the assembly of novel and diversified benzo-fused N-heterocycles mediated by the biomass-derived N-arylated 2-aminophenol (1) has been established. Four kinds of benzo-fused N-heterocycles with six- to eight-membered ring systems, including N-arylated dibenzo[b,e][1,4]oxazepin-11(5H)-ones (4), acridones (5), 7,12-dihydrodibenzo[b,e][1,4]oxazocin-6H-ones (6) and dibenzo[b,f]azepin-10(11H)-ones (7) have been efficiently synthesized in good to excellent yields, respectively. This process is comprised of the N-arylation reaction between N-arylated 2-aminophenols (1) and 2-halogenated benzoic or phenylacetic acids to afford a series of mutli-functionalized triarylamines (3), followed by chemo- and regio-selective intramolecular lactonization or acylation under mild conditions.

Graphical abstract: A biomass-involved strategy for the synthesis of N-arylated dibenzo[b,e][1,4]oxazepin-11(5H)-ones, acridones, 7,12-dihydrodibenzo[b,e][1,4]oxazocin-6H-ones and dibenzo[b,f]azepin-10(11H)-ones

Supplementary files

Article information

Article type
Paper
Submitted
16 Oct 2014
Accepted
27 Nov 2014
First published
01 Dec 2014

RSC Adv., 2015,5, 5288-5294

Author version available

A biomass-involved strategy for the synthesis of N-arylated dibenzo[b,e][1,4]oxazepin-11(5H)-ones, acridones, 7,12-dihydrodibenzo[b,e][1,4]oxazocin-6H-ones and dibenzo[b,f]azepin-10(11H)-ones

E. Zhang, X. Zhang, W. Wei, D. Wang, Y. Cai, T. Xu, M. Yan and Y. Zou, RSC Adv., 2015, 5, 5288 DOI: 10.1039/C4RA12479K

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