Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

• Published in: ChemistrySelect (Weinheim) 2021-10, Vol.6 (38), p.10274-10322
• Main Author: Chandra, Prakash
• Format: Article
• Language: English
• Subjects: amine surrogates; ammoxidation; carboxylic acid surrogates; multicomponent reactions; N-alkylation; N-arylation
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202103035

Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis. Copper based homogeneous and heterogeneous catalysts effectively promote synthesis of heterocyclic amides by reacting carboxylic acid surrogates like aldehydes, ketones, esters, amides, alkanes, alkenes and alkynes with amine surrogates like amides, azides and thioamindes. Several other multifarious route like reductive amidation of nitro‐compounds, rearrangement of ketoximes, aldoximes, aminocarbonylation reactions, hydration of nitriles and coupling of nitriles with alcohols and amines. The resulting heterocyclic amides are used as multifarious agrichemicals, drugs and insecticides.