84258-33-3

Upstream product

• 201348-87-0 N-benzyl-2,2-dichloro-N-(2-phenylthiocyclohex-1-enyl)acetamide 
• 201348-84-7 N-benzyl-2,2,2-trichloro-N-(2-phenylthiocyclohex-1-enyl)acetamide 
• 4471-09-4 N-benzylcyclohexylimine 
• 108-94-1 cyclohexanone 
• 100-46-9 benzylamine 
• 768-17-2 2-oxocyclohexenylene acetic acid enol lactone 
• 932-03-6 1-Ethynyl-7-oxa-bicyclo[4.1.0]heptane 
• 27866-39-3 1-benzyl-4,5,6,7-tetrahydro-1H-indole 

Downstream Products

• 84258-41-3 1-Benzyl-7-chloro-1,4,5,6-tetrahydro-indol-2-one 
• 1001112-18-0 C₁₅H₁₄BrNO 
• 7135-32-2 1-benzylindolin-2-one 

Relevant academic research and scientific papers

Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids

A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine.

Short Total Synthesis of (±)-γ-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-γ-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.

3D-Printed Polypropylene Continuous-Flow Column Reactors: Exploration of Reactor Utility in SNAr Reactions and the Synthesis of Bicyclic and Tetracyclic Heterocycles

3D printing has the potential to transform the way in which chemical reactions are carried out due to its low-cost, ease-of-use as a technology and its capacity to expedite the development of iteratively enhanced prototypes. In this present study, we developed a novel, low-cost polypropylene (PP) column reactor that was incorporated into an existing continuous-flow reactor for the synthesis of heterocycles. The utility and solvent resistance of the printed devices were explored in SNAr reactions to produce substituted aniline derivatives and in the synthesis of bicyclic and tetracyclic heterocycles. Using this approach, a range of heterocyclic compounds was synthesised including the core structure of the natural product (±)-γ-lycorane and structurally complex compounds based on the tetracyclic core of the erythrina alkaloids.

Synthesis of novel 7-substituted 5,6-dihydroindol-2-ones via a Suzuki-Miyaura cross-coupling strategy

A versatile method for the synthesis of new 7-substituted 5,6-dihydroindol-2-ones is described. The synthetic strategy proceeds through the use of the established palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of halogenated indol-2-ones and a

Regiochemistry in radical cyclizations (5-endo versus 4-exo) of N-(2-phenylthio- and 2-phenylcyclohex-1-enyl)-α-halo amides

Bu3SnH-mediated radical cyclization of N-(2-phenylthiocyclohex-1-enyl)-α-halo amides was examined. Bromoacetamide 9a having no substituent α to the halogen atom cyclized exclusively in a 4-exo-trig manner, whereas the fully substituted haloamides 9c and 9e gave 5-endo-trig cyclization products. The mono-substituted haloamides 9b and 9d showed an intermediate behavior to give a mixture of 4-exo and 5-endo cyclization products. The results of experiments on the effect of reaction temperature indicated that at a low temperature, i.e. under kinetically controlled conditions, 4-exo-trig cyclization predominated. On the other hand, the 2-phenylcyclohex-1-enyl congeners 22b and 22c gave exclusively 5-endo cyclization products.

Effect of temperature on 5-endo- and 4-exo-trig radical cyclizations of N-vinylic α-halo amides

The radical 3a generated from N-vinylic trichloroacetamide 1a provided the 5-endo-trig cyclization product 2a in boiling toluene, whereas, at room temperature, gave the 4-exo-trig cyclization product 9. The results may be explained in terms of the reversi

β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton

N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.

Aromatization of Aliphatic Compounds. VII (1). Benzofuranones, Indoles and Oxindoles

2(4H)-5,6-Dihydrobenzofuranones 3 gave, when treated with pyridine hydrochloride at 200 deg, the corresponding arylacetic acids 1 in good yields, whereas the aza analogues, the tetrahydrooxindoles 6 gave indoles in poor yields.The oxidation products of 3 (11 and 13) and of 6 (12, 14 and 15) gave, with the same reagent, benzofuranones and oxindoles, respectively, both in good yields.