Heterocycles by cycloaddition. Part II. Cycloaddition–extrusion reactions of five-membered mesoionic compounds with benzyne: prepartion of benz[c]azole and benzo[c]thiophen derivatives
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 672-675
- https://doi.org/10.1039/p19760000672
Abstract
Several five-membered mesoionic compounds react with benzyne to give benzo-fused five-membered heterocycles [(2) and (5)] with a formal quinonoid structure. A bridged intermediate adduct (4c) was isolated from the reaction of benzyne with a mesoionic thiazol-4-one (3c). Pyrolysis of the adduct gave an isobenzothiophen (5a), whereas its photolysis led to an isoquinolone (7). The corresponding adduct S-oxide (4e) gave the isoquinolone (7) by both pyrolysis and photolysis.Keywords
This publication has 0 references indexed in Scilit: