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  • Title: Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway.
    Author: Sharma SK, Mandadapu AK, Kumar B, Kundu B.
    Journal: J Org Chem; 2011 Aug 19; 76(16):6798-805. PubMed ID: 21732650.
    Abstract:
    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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