102804-46-6

Upstream product

• 615-36-1 2-bromoaniline 
• 36278-22-5 1-cyclohexenoyl chloride 
• 636-82-8 cyclohexene-1-carboxylic acid 

Downstream Products

• 109686-66-0 Cyclohex-1-enecarboxylic acid (2-bromo-phenyl)-(2-trimethylsilanyl-ethoxymethyl)-amide 
• 4933-14-6 spiro[cyclohexane-1,3'-[3H]indol]-2'(1'H)-one 
• 102804-51-3 N-(2-bromophenyl)-N-methyl-1-cyclohexene-1-carboxamide 

Relevant academic research and scientific papers

Solid-phase synthesis of indol-2-ones by microwave-assisted radical cyclization

Solid-phase synthesis of indol-2-ones (2-oxindoles) by means of aryl radical cyclization of resin-bound N-(2-bromophenyl)acrylamides using Bu 3SnH is described. Among various solvents tested, DMF was found to be the best choice for the radical cyclization inducing a reagent concentration effect of the polymer support. The reaction proceeded smoothly under microwave irradiation to give the desired indol-2-ones within a very short reaction time in comparison to conventional thermal heating. In this reaction, various indol-2-ones were synthesized by using commercially available 2-bromoanilines and acryloyl chloride derivatives.

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.