title: Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway.
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.
authors: Medicinal & Process Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226001, India.
authors: Sudhir K
authors: SK
authors: Sharma
authors: Anil K
authors: AK
authors: Mandadapu
authors: Brijesh
authors: B
authors: Kumar
authors: Bijoy
authors: B
authors: Kundu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001381:Azepines; D007211:Indoles; D020005:Propanols; C540210:azepino(4,5-b)indolone; D007455:Iodine; C028255:propargyl alcohol