Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 16, Pages 6798-6805Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201228t
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- CSIR, New Delhi, India
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An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.
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