Reaction of (E)-3-(Benzo[d][1,3]dioxol-5-yl)-2- Cyanoacryloyl Chloride with Nucleophilic Reagents Containing Nitrogen and Sulfur

Synthesis of novel 2-propenoyl amides, esters, heterocyclic compounds and their screening as antifungal and antibacterial agents

“…In continuation of our efforts to study the reactivity of 2-propenoyl chlorides towards some nitrogen and oxygen nucleophilic reagents [20][21][22][23], we reported herein, the synthesis of a new compound, (E)2-cyano-3-(2,4-dichloro phenyl)acryloyl chloride 3 via the common route condensation of 2,4-dichlorobenzaldehyde with ethyl cyanoacetate in the presence of piperidine, to give the corresponding (E)-ethyl 2-cyano-3-(2,4-dichlorophenyl) acrylate, 1, [24]. Hydrolysis of 1 in alcoholic solution of sodium hydroxide (1:1 mole) gave (E)-2-cyano-3-(2,4-dichlorophenyl)acrylic acid, 2, [25].…”

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

“…[ 23,24 ] Recently, it was reported that 2‐cyano‐3‐arylacryloyl chlorides were utilized as building blocks for several heterocyclic skeletons like benzimidazoles, benzoxazoles, benzothiazoles, benzothiazepines, benzoxazinones, pyrimidinethiones, oxadiazoles, and pyrazoles with significant pharmaceutical potency. [ 25–29 ] Based on these facts, we aimed, in this work, to construct new pyrazole‐based heterocycles, for example, oxadiazepine, pyridopyrimidine, thiadiazolopyrimidine, and benzoxazinone derivatives, starting from acryloyl chloride derivative, and evaluate their antiproliferative efficacy against liver and breast cancer cells, as well as, the molecular docking study, using MOE (molecular modeling environment), to infer the binding free energies of the studied compounds toward the human cyclin‐dependent kinase 2.…”

Synthesis and antimicrobial evaluation of some new quinazolin-4(3H)-one derivatives

“…In continuation of our interest in synthesis and studying the reaction behavior of benzoxazinones and quinazolinones [16][17][18][19][20] we reported herein the behaviour of the benzoxazinone derivative, 3, with some active methylene compounds as carbone nucleophile, so the benzoxazinone derivative, 3, was reacted with ethyl cyanoacetate and/or malononitrile in pyridine to give 2-(2-(anthracen-9-yl)-1-benzamidovinyl)-4-oxo-3,4-dihydro-quinoline-3-carboxylic acid, 6, via ring opening and ring closure of the benoxazinone derivative, 3, followed by hydrolysis of the cyano or the ethylester group to the carboxylic group. The structure of compound 6 was confirmed from the 1 H NMR spectrum showing the δ value at 12.48 ppm for singlet, one proton, corresponding to the carboxylic hydrogen and disappeared by D2O, hydrazinolysis of compound 3 in boiling ethanol afforded the triazinoquinqzolinone derivative, 7, according to the following mechanism (Scheme 3).…”