title: Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes.
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.
authors.affiliation: School of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, Japan. miyabe@huhs.ac.jp.
authors.forename: Hideto
authors.initials: H
authors.lastname: Miyabe
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis*; D001578:Benzopyrans / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D003374:Coumarins / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D005559:Formamides / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D014966:Xanthenes / Q000138:chemical synthesis*
chemical_list: D000447:Aldehydes; D001555:Benzene Derivatives; D001572:Benzofurans; D001578:Benzopyrans; D003374:Coumarins; D005559:Formamides; D014966:Xanthenes; D010100:Oxygen
keywords: arynes; multi-component reaction; oxygen heterocycles; synthesis