Practical multi-component synthesis of di- or tri-aryl (Heteraryl) substituted 2-(pyridin-2-yl)imidazoles from simple
Xiao-Jin Wu1, Ran Jiang, Xiao-Ping Xu
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Abstract:
A convenient and highly efficient multicomponent protocol has been developed for the synthesis of various poly-substituted 2-(pyridin-2-yl)imidazoles from 2-cyanopyridine, corresponding aromatic aldehydes, and NH(4)OAc/primary amine. Notably, tri-substituted 2-(pyridin-2-yl)imidazoles were highly yielded when aromatic primary amines were used as substrates, but both di- and tri-substituted 2-(pyridin-2-yl)imidazoles were obtained in one pot when some aliphatic primary amines were used as substrates.
Related Concept Videos
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...
Basicity of Heterocyclic Aromatic 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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism


