Intramolecular addition of vinyl and aryl radicals to oxime ethers in the synthesis of five-, six- and seven-membered ring systems

Abstract

The oxime ethers 2a–e have been cyclised with Bu3SnH to the alkoxyamino-3-methylidenechromanes 3a–e. Seven-membered ring formation was observed when the oxime ethers 7a, b were converted into the dibenzo[b,e]oxepines 8a, b under similar conditions. 1-Methoxyaminoindanes 12a, b were produced from the cyclisation of the substrates 11a, b and the cis-fused cyclic products 15a, b and 18 were obtained from compounds 14a, b and 17, respectively.