Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization Pathway
SK Sharma, AK Mandadapu, B Kumar… - The Journal of Organic …, 2011 - ACS Publications
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 I2 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 …
via a three-component reaction of indole-2-carboxamides, 1, 3-disubstituted propargyl
alcohols, and I2 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 …
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 I2 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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