68639-02-1

Upstream product

• 1620143-04-5 1-benzyl-2-phenyl-2,3,6,7-tetrahydro-1H-indol-4(5H)-one 
• 1380499-39-7 2-oxo-1-(6-oxocyclohex-1-en-1-yl)-2-phenylethyl acetate 
• 100-46-9 benzylamine 
• 1380499-34-2 2-(1-hydroxy-2-oxo-2-phenylethyl)cyclohex-2-en-1-one 

Downstream Products

• 66354-67-4 4-methyl-2-phenyl-1H-indole 
• 52604-15-6 1-benzyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

An Efficient Route to Highly Substituted Indoles via Tetrahydroindol-4(5H)-one Intermediates Produced by Ring-Opening Cyclization of Spirocyclopropanes with Amines

An efficient route to highly substituted indoles was developed. It included regioselective functionalization of tetrahydroindol-4(5H)-ones, prepared by ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines, and subsequent oxidation. The 6-substituted indoles were synthesized from a readily available 5-substituted cyclohexane-1,3-dione-2-spirocyclopropane. The synthesis of 5- and 7-substituted indoles was achieved by regioselective electrophilic alkylation of tetrahydroindol-4(5H)-one, followed by oxidation. The 4-substituted indoles were synthesized by nucleophilic alkylation of the corresponding pyrrole derivative, which was prepared by partial oxidation of tetrahydroindol-4(5H)-one, and sequential oxidation. The synthesis of 4-substituted indoles was also accomplished by palladium-catalyzed coupling of 4-hydroxyindole-derived triflates. Furthermore, the synthesis of 4,5,6,7-tetrasubstituted indoles was achieved by using these regioselective alkylations.

Versatile synthesis of 2-(substituted phenyl)-6,7-dihydro-1H-indol-4(5H)- ones from Morita-Baylis-Hillman acetates of 2-oxo-2-(substituted phenyl)acetaldehyde

A versatile synthesis of 2-(substituted phenyl)-6,7-dihydro-1H-indol-4(5H)- ones from adducts of the Morita-Baylis-Hillman reaction between 2-oxo-2-(substituted phenyl)acetaldehydes and cyclohex-2-enone under mild conditions is described. Application of adducts prepared by the Morita-Baylis-Hillman reaction between 2-oxo-2-(substituted phenyl)acetaldehydes and cyclohex-2-enone for the synthesis of 2-(substituted phenyl)-6,7-dihydro- 1H-indol-4(5H)-ones has been described. Copyright