Reaction of Benzo [b] furan and 1-Acylindoles with Iodine Azide

Abstract

Reaction of benzo [b] furan with iodine azide gives in high yield a mixture of cis-and trans-2, 3-diazido-2, 3-dihydrobenzo [b] furans, both of which, upon treatment with alkali, are converted to 3-azidobenzo [b] furan. Similar reaction of 1-benzoyl-and 1-tosyl-indoles with iodine azide affords high yields of cis-and trans-1-benzoyl-and 1-tosyl-2, 3-diazidoindolines. Stereochemical assignment of the adducts is made on the basis of nuclear magnetic resonance spectroscopy.