A Novel Synthesis of 3-Aryl-2,6-dicyano-5-methylanilines via Reaction between Nitrostyrenes and Malononitrile

Abstract

A novel and simple synthesis of 3-aryl-2,6-dicyano-5-methylanilines is described. Reactions between nitrostyrenes and excess malononitrile in the presence of sodium carbonate in 80% ethanol proceeded at room temperature to afford the aromatic products in good yields. A mechanism for the formation of the products is proposed.

Efficient three-component one-pot synthesis of steroidal polysubstituted anilines

“…These observations may set records for highly upfield chemical shifts of aromatic carbons in a benzene ring. The nitrile assignments for 2,6-dicyanoanalines by Adib et al may be incorrect [16]. Selected chemical shifts of compound 4a are shown in Fig.…”

“…It seems that such ring system has escaped from our attention in drug discovery programs. In fact, benzene scaffolds with suitable substituents have been reported to possess diverse biological properties and can also serve as important synthetic intermediates [13][14][15][16]. Additionally, polysubstituted biphenyl derivatives are also found in numerous natural products and pharmaceutical agents [17][18][19][20][21][22].…”

Synthesis of Fluorescent 2,6‐Dicyano‐3,5‐Disubstituted Anilines Using Cellulose Sulfuric Acid in Aqueous Media

“…Compound 2b has attracted a lot of interest. It has been the subject of many studies in recent years, and some approaches have been reported for its synthesis . Here, we report the Cellulose‐SA catalyzed synthesis of 2b using 1‐phenylbutane‐1,3‐dione as reactant in H 2 O as solvent.…”

CoFe2O4@SiO2‐PA‐CC‐guanidine nanoparticles: A novel, efficient, and recyclable catalyst for the synthesis of 3,5‐disubstituted‐2,6‐dicyanoaniline derivatives

“…Polysubstituted benzenes are important groups in organic chemistry. These compounds have specific applications in the natural products chemistry, medicinal chemistry, and material chemistry . However, their synthesis remains an important challenge.…”