Synthesis of cyano-substituted γ-lactams through a copper-catalyzed cascade cyclization/cyanation reaction

Abstract

A convenient copper-catalyzed cascade cyclization/cyanation reaction for the construction of cyano-containing γ-lactams was developed. The protocol employed TMSCN as the cyano source and proceeded in water under simple conditions. Mechanistic...

One-pot access to 11-methyl-6H-indolo[2,3-b]quinolines via iodine-mediated annulation of indoles with 2-vinylanilines and evaluation of their biological activities

“…14 Meanwhile, various reagents based on iodine are constantly being developed and applied. 15 As continuation of our ongoing research on organoiodine 16 and N-heterocycles, 17 herein, we now present our discoveries in iodine-mediated efficient synthesis of diverse 11-methyl-6 H -indolo[2,3- b ]quinolines via annulation of indoles with 2-vinylanilines. Besides, our newly synthesized 11-methyl-6 H -indolo[2,3- b ]quinoline derivatives showed promising cytotoxic and antiviral activities in biological evaluations.…”

Silver-Catalyzed Cascade Radical Bicyclization Reaction: An Atom- and Step-Economical Strategy Accessing γ-Lactam Containing Isoquinolinediones

“…In recent years, radical cascade cyclization has come to the fore as a valuable tool for constructing complex molecules due to its high atom- and step-economy . Previously, many research groups, including our own, conducted a series of studies on the formation of γ-lactam derivatives through radical cascade cyclization of N -phenyl-4-pentenamides . Recently, we have introduced a new radical cascade bicyclization platform that allows a γ-lactam carbon radical, generated from an amidyl radical-initiated cascade 5-exo-trig cyclization, to add to N- methyl- N -phenylacrylamides under silver catalysis to form two five-membered nitrogen heterocycles.…”

Cobalt-Catalyzed Aerobic Aminocyclization of Unsaturated Amides for the Synthesis of Functionalized γ- and δ-Lactams

“…with trimethylsilyl cyanide to provide cyano-containing γlactams has been reported. 14 In previous studies, we disclosed manganese-and cobaltcatalyzed cyclization reactions of unsaturated hydrazones to access a range of complex and highly functionalized pyrazolines. 15 We subsequently became interested in expanding the transformation beyond hydrazones.…”

“…Additionally, photoredox catalysis has been employed to effect aminofluorosulfonylation and amidoarylation of unactivated olefins . Recently, aminocyanation of N -aryl-pent-4-enamides with trimethylsilyl cyanide to provide cyano-containing γ-lactams has been reported …”

“… 13 Recently, aminocyanation of N -aryl-pent-4-enamides with trimethylsilyl cyanide to provide cyano-containing γ-lactams has been reported. 14 …”