Environmental-friendly one-pot cascade synthesis of 3-cyanopiperidin-2,6-diones

Abstract

3-Cyanopiperidin-2,6-diones are key intermediates in the synthesis of several drugs and natural products. We developed onepot synthesis of 3-cyanopiperidin-2,6-diones by Knoevenagel condensation of cyanoacetic acid and aldehydes, followed by addition of cyanoacetic acid, Achmatowicz reaction and decarboxylation. We tested a wide range of aliphatic and aromatic aldehydes. Products were obtained under simple, environmentally friendly conditions and in yields up to 99%. Substrates were stirred in toluene at reflux, and filtered through short pad of silica gel, and the product was purified by recrystallization.

Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

“…It represents a crucial intermediate of fine chemical industry such as medicine, agrochemicals, and dyes [21,23]. It is beneficial for the production of esters, amides, acids, and nitriles and is used as an intermediate for the synthesis of 3-cyanopiperidin-2,6-diones [24], substituted tetrahydroquinolines [25] 2-amino-4,6dimethoxypyrimidine an intermediate for sulfonylurea herbicides, and the insecticide flufenitrile [26]. Based on their biological and synthetic impact, many asymmetric strategies have been adopted for the preparation of chiral amines in the enantiopure form [2,8].…”

Potassium Modified Carbon Nitride as a Highly Efficient and Recyclable Catalyst in Knoevenagel Reaction

“…As the core part of various chemical reactions, catalysts play a pivotal role in the reaction process. The appropriate design and careful selection of heterogeneous catalysts can considerably improve the organic transformations (Gao et al 2020;Paprocki et al, 2020).…”