Related Experiment Video
Updated: Jun 13, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
3-Azetidinylpiperidine-4-alkylidenemalononitrile and Related Building Blocks
Juan M Sanfiel1, Andrew T McCabe1, Aleksandra Nilova2
1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
Abstract:
Cyclobutanes, azetidines, and oxetanes have become more prevalent as structural features on pharmaceutical leads and drugs due to their unique physicochemical and biological properties. Substitution of (hetero)cyclobutanes in a stereocontrolled fashion with pharmaceutically relevant functionality is still a modern challenge. Described herein is a method for constructing quaternary (hetero)cyclobutanes and linking them to other (hetero)cycles via an allylic alkylation/exocyclic strain-release Cope rearrangement. The one- or two-step sequence can yield uniquely linked heterocycles bearing an alkylidenemalononitrile functional group, which can be readily transformed into amides diastereoselectively. This study includes optimization and scope studies of the allylic alkylation/[3,3] sequence, enantioselective optimization using asymmetric allylic alkylation, and functional group interconversion studies to yield densely substituted drug-like scaffolds.
More Related Videos
12:02An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
Published on: November 2, 2016
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Nomenclature of Primary Amines
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...