3720-46-5

Upstream product

• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 109-77-3 malononitrile 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 134426-13-4 4-amino-2,6-dioxo-5-(p-ethoxycarbonyl-phenylhydrazono)-1,2,5,6-tetrahydropyrid-3-yl-pyridiniumchlorid 
• 134425-96-0 2-(4-carbethoxyphenyl)-4-cyano-5-morpholino-1-yl-2H-[1,2,3]triazole 
• 134426-10-1 2-(p-carbethoxyphenyl-hydrazono)-2-cyan-N-chloracetyl-acetamid 
• 134425-88-0 2-(p-carbethoxyphenylhydrazono)-2-cyan-N,N-(3-oxopentamethylen)-acetamidin 

Relevant academic research and scientific papers

Synthesis of 2-arylamino-3-cyanoquinolines: Via a cascade reaction through a nitrilium intermediate

A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of aryldiazonium salts and malononitrile, which undergoes intermolecular amination, Knoevenagel condensation, and then aromatization to yield the desired compound in moderate to good yields. This methodology features a quick assembly of C2 and C3 functionalized quinolines.

Multistep flow synthesis of 5-amino-2-aryl-2h-[1,2,3]-triazole-4-carbonitriles

1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.