Synthesis of a novel heterocyclic scaffold utilizing 2-cyano-N-(3-cyano-4,6-dimethyl-2-oxopyridin-1-yl) acetamide

Abstract

2-Cyano-N-(3-cyano-4,6-dimethyl-2-oxopyridin-1-yl)acetamide (3) was prepared via two routes and its reactions with various aldehydes and diazonium salts were studied. When compound 3 was treated with arylidenemalononitrile in either ethanol or dioxane using piperidine as a catalyst in a trial to prepare bispyridone derivatives 7, there was no reaction and the reason for this was investigated using molecular modeling. Furthermore, coumarin derivatives 9 and 10 were prepared by reaction of acetamide 3 with salicylaldehyde derivatives. Finally, aminopyrazole derivatives 15 were synthesized by reaction of acetamide 3 with N,N-dimethylformamide dimethyl acetal (DMFDMA) then with hydrazine derivatives and their mechanisms was discussed.

Design, synthesis and docking studies of novel thiazole derivatives incorporating pyridine moiety and assessment as antimicrobial agents

“…The precursor N -aminopyridone 1 was synthesized from the reaction of acetylacetone with cyanoacetohydrazide in EtOH containing piperidine at reflux temperature 36 . Solution of 1 in conc.…”

“…2 ). Compounds containing the pyridine pattern have a wide range of biological profiles including antimicrobial 31 – 36 , anti-viral 37 , 38 , antioxidant 39 , antidiabetic 40 , anticancer 41 – 43 , anti-inflammatory agents 44 , 45 . For all these benefits related to thiazole and pyridine derivatives and following our work 46 – 50 , we report here the synthesis of a new library of thiazole derivatives from 1-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2 H )-yl)thiourea 2 .…”

Synthesis of 4‐Hydroxy‐2‐pyridinone Derivatives and Evaluation of Their Antioxidant/Anticancer Activities

“…Nowadays, the pyridine ring is of great importance to biologists as well as to chemists for its interesting and diverse biological activities, in addition, it is found in several natural products and pharmaceutical molecules. Furthermore, the pyridine skeletons have emerged as integral backbones of over 7000 existing drugs [1,2] . Also, the pyridine ring is an integral part of anti‐inflammatory and anticancer agents [3–8] .…”

Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3‐(1,4‐Dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile as Precursors

“…In addition, coumarin derivatives occupied significant site either in natural products or in organic synthesis due to their exhibit plenty pharmacological activities [25][26][27]. Based on the earlier information and in continuing with our previous work [28,29], we have designed and synthesized coumarin, pyrane, pyrazole, and hydrazone derivatives bearing phthalazine moiety.…”