Related Experiment Video
Updated: Jan 9, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of Indenopiperidinone Derivatives Achieved through the Aza-Semipinacol-Type Rearrangement of
Magdalena M Lubowicz1,2, Tomasz J Idzik1,2, Łukasz Struk1,2
1Faculty of Chemical Technology and Engineering, Department of Organic and Physical Chemistry, West Pomeranian University of Technology in Szczecin, Al. Piastów 42, 71-065 Szczecin, Poland.
Abstract:
The synthesis of 2,4,4a,9-tetrahydro-3H-indeno[2,1-c]pyridin-3-ones 7 is achieved through the aza-semipinacol-type rearrangement of readily available iodobenzomorphanones when treated with silver salts. A comprehensive study was performed on the optimization of the synthesis of iodobenzomorphans and subsequent rearrangement products, while addressing the scope and limitations of both reactions. It has been shown that the resulting indeno[2,1-c]pyridine-3-ones, acting as enelactams, are suitable precursors for further stereoselective functionalization, e.g., reduction, using an NaBH4/NiCl2 system, and arylation activated by TIPSOTf.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...