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Catalyst‐Controlled Chemodivergent Annulation to Indolo/Pyrrolo‐Fused Diazepine and Quinoxaline
Author(s) -
Dhole Sandip,
Chiu WeiJung,
Sun ChungMing
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900088
Subject(s) - quinoxaline , chemistry , diazepine , annulation , catalysis , indole test , combinatorial chemistry , medicinal chemistry , carbene , organic chemistry , ring (chemistry)
Catalyst‐controlled chemodivergent annulation between o ‐indolo anilines and diazo compounds has explored for the synthesis of indolo‐fused diazepine and quinoxaline. Under the Rh(III) catalyst, reaction proceeded through the free amine assisted C2−H activation followed by amidation leading to the diazepino[1,7‐ a ]indole in a highly selective manner. While with Ru(II) catalyst, reaction involves formation Ru−carbene complex followed by −NH 2 group insertion and cascade cyclization via metallo‐ene type reaction, β‐hydride elimination to furnish the indolo[1,2‐ a ]quinoxaline as the predominating product. This strategy directs modular approach towards the construction of unique indolo‐fused diazepine/quinoxaline as well as pyrrolo‐fused diazepine/quinoxaline scaffolds in excellent yields.