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

Hideto Miyabe
2015 Molecules  
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
more » ... 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.
doi:10.3390/molecules200712558 pmid:26184140 fatcat:xlg275t6f5flloejajuddbr23q