Uses of Piperonal in the Synthesis of Novel Prop-2-Enoyl Amides, Esters, Heterocyclic Systems and Study of their Antibacterial Activities

Abstract

Novel (E)-3-(benzo[d][1,3]dioxol-5-yl)-2-cyanoacryloyl chloride 4 was condensed with several mono-; 1,2-; 1,3- and 1,4-bi-nucleophilic reagents containing nitrogen and oxygen to give new 2-propenoylamide and ester derivatives. Some of these amides cyclised under the reaction conditions and/or with POCl3 to give new derivatives of heterocyclic systems. Antibacterial activities were tested for nine of these products.

Synthesis and antimicrobial activity of some new coumarin and dicoumarol derivatives

“…A chemical proof for the suggested structure is gained by preparing an authentic sample through reacting of piperonal and/or p ‐anisaldehyde with hydrazine hydrate. It was identical in all respects mp, mmp, and TLC with compounds 11a,b . The mechanistic pathway for the formation of compound 11 is depicted in Scheme .…”

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 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).…”