66558-33-6

Upstream product

• 21731-13-5 (E)-3-Benzylamino-but-2-enoic acid ethyl ester 
• 130-15-4 [1,4]naphthoquinone 
• 1020-67-3 ethyl 3-(benzylamino)crotonate 
• 1439385-95-1 (E)-ethyl 3-(benzylamino)-2-(1,4-dioxo-1,4-dihydro-naphth-2-yl)but-2-enoate 
• 141-97-9 ethyl acetoacetate 
• 100-46-9 benzylamine 

Downstream Products

• 66558-31-4 ethyl 1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate 

Relevant academic research and scientific papers

Nenitzescu Synthesis of 5-Hydroxyindoles with Zinc, Iron and Magnesium Salts in Cyclopentyl Methyl Ether

In this work, mild Lewis acids and low environmental impact solvents were investigated for Nenitzescu synthesis. Cyclopentyl methyl ether can be used at room temperature in substitution of halogenated solvents with zinc, iron and magnesium salts as homogeneous catalysts to give 5-hydroxyindoles in fair to good yields. The reaction features a straightforward workup and excellent solvent recycle.

A new CAN-catalyzed domino process related to the Nenitzescu reaction: Very concise access to fused ortho-indolequinones from simple precursors

The CAN-catalyzed three-component reaction between primary amines, β-ketoesters and naphthoquinone in ethanol at room temperature afforded as the main products the corresponding Michael adducts, oxidized to the quinone stage. When these compounds were refluxed in ethanol in the presence of CAN, they afforded tricyclic ortho-quinones derived from the benzo[g]indole-4,5-dione framework via a domino mechanism comprising a sequence of 5-exo-trig cyclization, elimination, Michael addition, oxo-enol tautomerism and hydroquinone oxidation individual steps.

Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments

The CAN-catalyzed three-component between reaction between primary amines, β-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g] indole systems through a γ-alkylation/ring-closing metathesis sequence. The Royal Society of Chemistry 2010.