Reaction of benzo [b] furan and 1-acylindoles with iodine azide
Y TAMURA, MWOO CHUN, S KWON… - Chemical and …, 1978 - jstage.jst.go.jp
Y TAMURA, MWOO CHUN, S KWON, MB SAID, T OKADA, M IKEDA
Chemical and Pharmaceutical Bulletin, 1978•jstage.jst.go.jpReaction 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-benzoy1—and 1-tosy1—indoles
with iodine azide affords high yields of cis-and trans-I-benzoyl-and 1-tosy1—2, 3-diazido—
indolines. Stereochemical assignment of the adducts is made on the basis of nuclear
magnetic resonance spectroscopy.
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-benzoy1—and 1-tosy1—indoles
with iodine azide affords high yields of cis-and trans-I-benzoyl-and 1-tosy1—2, 3-diazido—
indolines. Stereochemical assignment of the adducts is made on the basis of nuclear
magnetic resonance spectroscopy.
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-benzoy1—and 1-tosy1—indoles with iodine azide affords high yields of cis-and trans-I-benzoyl-and 1-tosy1—2, 3-diazido—indolines. Stereochemical assignment of the adducts is made on the basis of nuclear magnetic resonance spectroscopy.
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