2406-10-2

Upstream product

• 175658-16-9 α-(phenylthio)-N-methyl-N-phenylacetamide 
• 108-98-5 thiophenol 
• 100-61-8 N-methylaniline 
• 3335-86-2 3-hydroxy-1-methyl-indolin-2-one 

Downstream Products

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 63955-65-7 1-methyl-3,3-di(phenylthio)indolin-2-one 

Relevant academic research and scientific papers

Electrophilic Amide Allylation of 3-Heterosubstituted Oxindoles: A Route to Spirocyclic 2-Oxindoles Containing the α-Methylene-γ-butyrolactam Structure

This article reports a new route to access spirocyclic 2-oxindoles containing the α-methylene-γ-butyrolactam structure via “electrophilic amide allylation”. The key reaction was accomplished by using acetoxy methacrylamides and tetrakis(triphenylphosphine)palladium as catalyst, affording a variety of the amide allylated products in excellent yields. The successful cyclization of these products has demonstrated the potential utility of this approach to offer a practical synthesis of spirocyclic oxindoles.

Formation of N-heterocycles by the reaction of thiols with glyoxamides: Exploring a connective Pummerer-type cyclisation

The reaction of thiols with glyoxamides provides a convenient method for the generation of thionium ions and the initiation of Pummerer-type reactions. When the glyoxamides contain tethered aromatic nucleophiles, N-heterocycles are formed by a thionium ion cyclisation. The scope and mechanism of the connective Pummerer-type process has been investigated using a range of thiols, Lewis acids and both mono- and bis-glyoxamides. The utility of the process has been illustrated in a synthesis of the indoloquinoline natural product, neocryptolepine. The Royal Society of Chemistry 2009.

Exploring a new, connective Pummerer reaction: Formation of oxindoles by the reaction of thiols with glyoxamides

The reaction of a range of thiols with mono- and bis-glyoxamides derived from secondary anilines, triggers a new, connective Pummerer cyclisation process and leads to the formation of oxindoles. The Royal Society of Chemistry.

Electroorganic synthesis using a fluoride ion mediator under ultrasonic irradiation: Synthesis of oxindole and 3-oxotetrahydroisoquinoline derivatives

(Equation Presented) Anodic intramolecular cyclization of α-(phenylthio)acetamides using a fluoride ion mediator was realized. Under ultrasonic irradiation, cyclization was accelerated markedly to give desired cyclized products in moderate to good yields.

Fluorination of sulfanyl amides using difluoroiodoarene reagents

A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon-sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14-19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41-43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45-47.

Studies on the oxidation and fluorination of α-phenylsulfanylacetamides using difluoroiodotoluene

α-Phenylsulfanylacetamides are fluorinated in the α-position when treated with difluoroiodotoluene (DFIT) in a fluoro-Pummerer reaction. For N- phenyl amides an intramolecular Friedel-Crafts reaction may compete and produce heterocycles. (C) 2000 Elsevier Science Ltd.