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Molecules 2015, 20(7), 12558-12575; doi:10.3390/molecules200712558

Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes

School of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, Japan
Academic Editor: Hiroto Yoshida
Received: 17 June 2015 / Revised: 7 July 2015 / Accepted: 8 July 2015 / Published: 9 July 2015
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)

Abstract

Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes into the C=O bond gives the unstable intermediates, [2 + 2] cycloaddition-type adducts, which can be easily converted into a variety of oxygen atom-containing heterocycles in a single operation. In this review, the syntheses of oxygen heterocycles, such as coumarin, chromene, xanthene, dihydrobenzofuran and benzofuran derivatives, via the insertion of arynes into the C=O bond of aldehydes or formamides are summarized. View Full-Text
Keywords: oxygen heterocycles; arynes; synthesis; multi-component reaction oxygen heterocycles; arynes; synthesis; multi-component reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Miyabe, H. Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes. Molecules 2015, 20, 12558-12575.

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