102804-54-6

Upstream product

• 102804-51-3 N-(2-bromophenyl)-N-methyl-1-cyclohexene-1-carboxamide 
• 68557-32-4 cyclohexanecarboxylic acid N'-phenylhydrazide 
• 19493-09-5 Methylenetriphenylphosphorane 
• 591219-72-6 N-(2-iodophenyl)-N-methylcyclohexanecarboxamide 
• 163273-48-1 N-(2-bromophenyl)-N-methylcyclohexanecarboxamide 

Relevant academic research and scientific papers

Synthesis of indoles via alkylidenation of acyl hydrazides

Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.

Diethylphosphine oxide (DEPO): High-yielding and facile preparation of indolones in water

(Matrix presented) Indolones are prepared in excellent yield at 80°C in water by radical reaction (aryl radical formation, hydrogen atom abstraction, cyclization, and rearomatization) mediated by the reagent diethylphosphine oxide (DEPO). The reaction fea

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.

Non-toxic ligands in samarium diiodide-mediated cyclizations

Samarium diiodide-mediated cyclizations of aryl radicals carried out in the presence of several nitrogen ligands (triethylamine, 1,8-diazabyciclo[5.4.0]undec-7-ene and 1,1-3,3-Tetramethylguanidine) are described. The yields and the selectivities observed are comparable to the ones obtained by using hexamethylphosphoramide.