102804-51-3

Upstream product

• 102804-46-6 N-(2-bromophenyl)-1-cyclohexene-1-carboxamide 
• 74-88-4 methyl iodide 
• 636-82-8 cyclohexene-1-carboxylic acid 
• 615-36-1 2-bromoaniline 
• 36278-22-5 1-cyclohexenoyl chloride 
• 6832-87-7 2-bromo-N-methylaniline 

Downstream Products

• 102804-54-6 1′-methylspiro[cyclohexane-1,3′-indolin]-2′-one 
• 23824-50-2 cyclohexanecarboxylic acid methylphenylamide 
• 52514-10-0 5-Methyl-6a,7,8,9,10,10a-hexahydro-5H-phenanthridin-6-one 
• 163273-48-1 N-(2-bromophenyl)-N-methylcyclohexanecarboxamide 

Relevant academic research and scientific papers

Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions

A nickel-catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious-metal catalysis.

Concise synthesis of tetrahydrophenanthridone by palladium reagent

Heck reaction of N-(2-halophenyl)-N-methyl-1-cyclohexene-1carboxamide (1) and 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide (4) using a palladium reagent under several reaction conditions was examined. Reaction of 4 using Pd(OAc)2, DPPP, and Bu3P afforded tetrahydrophenanthridone (5) in excellent yield.

An Efficient Synthesis of Spiro via Radical Cyclisation

Treatment of the o-bromo-N-acryloylanilides (4) with tri-n-butylstannane leads to the formation of 3-substituted- and 3,3-disubstituted-2-oxindoles (5) in high yield.