Branch-Selective Synthesis of Oxindole and Indene Scaffolds: Transition Metal-Controlled Intramolecular Aryl Amidation Leading to C3 Reverse-Prenylated Oxindoles

Abstract

In an effort to access biologically important scaffolds, a concise branch-selective synthesis of C3 tertiary oxindoles by Cu(I)-catalyzed aryl amidation and 2,2-dimethyl indene by Pd(0)-catalyzed Heck cyclization has been accomplished from acyclic reverse-prenylated intermediates. Oxindole C3-enolate generation using NaH followed by alkylation in the presence of appropriate electrophiles provides a novel route to quaternary C3 reverse-prenylated oxindoles.

Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine

“…The amides are generated in short time scales, in high yield and with no complex post VFD operations required, with the product simply collected, washed with 2 M HCl, dried and recrystallized if obtained as a solid. In furthering this flow methodology, other factors were subsequently explored, namely, the use of an inert atmosphere of argon blanket over the film to circumvent mass transfer of moisture from air into the thin film, which could hydrolyze the acyl chloride, and the use of pyridine as the base, which is common in acylation reactions 23. 24 However, the effect on the yield was minimal (see the Supporting Information).…”

“…In furthering this flow methodology, other factorsw ere subsequently explored, namely,t he use of an inert atmosphere of argon blanket over the film to circumvent mass transfer of moisture from air into the thin film, which could hydrolyzet he acyl chloride, and the use of pyridine as the base, which is common in acylation reactions. [23,24] However, the effect on the yield was minimal (see the Supporting Information). Some subtle features related to flow rate were also revealed in this exploratory work.…”

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

“…Starting from 1a and 1a-alike cMAVIs, our structurally diversified coupling products 4 could be transformed into different series of heterocyclic fragments ( Figure 4 ). 4aa-4ag underwent palladium-catalyzed intracellular C-N formation to accomplish the indole ring construction in series 1 compounds (5a-5g) ( Bugaenko et al., 2018 ; Ignatenko et al., 2010 ). Meanwhile, the terminal vinyl double bond in 4aa could be used as an acceptor for halogenation ( Meimetis et al., 2014 ; Song et al., 2013 ).…”

Crystal structure of N-(1-benzyl-2-oxoindolin-3-yl)-N-p-tolylbenzofuran- 2-carboxamide, C31H24N2O3

“…We have established aP d-catalyzedintramolecularamidation of aryl bromides using palladium acetate-BINAP [5] as the catalyst furnishing the novel conjugates of N-phenylbenzofuran-2-carboxamides with a2 -oxindole [6] linked through aC-N single bond. The crystal structure analysis of the title compound revealed that geometric parameters of the title compound are in the normalranges.…”