Cyanoacetylurea in Heterocyclic Synthesis: A Simple Synthesis of Heterocyclic Condensed Uracils

Abstract

The condensation products of cyanoacetylurea with carbonyl compounds were utilized to prepare fused uracils through the intermediate formation of o-aminoureidocarbonyl heterocycles.

Synthesis with Docking Studies of Novel Heterocycles as Antimicrobial Agents Utilizing 2-Cyano-N-arylacetamide.

“…Antimicrobial activity [6][7][8] The newly synthesized compounds were screened for their antibacterial activity against Escherichia coli (Gram negative bacteria) and Staphylococcus aureus (Gram positive bacteria) by the disc diffusion method, and for their antifungal activity against Aspergillus flavus and Candida albicans in DMSO by the agar diffusion method.…”

“…[1-3] 2-Cyanoacetamide moieties have found as vital synthons in the synthesis of many active biological heterocyclic systems such as quinoxalinones, pyridines, thiazoles and pyrimidines. [4][5][6][7][8][9] So, our interested work herein is focusing on using N-(4-substitutedphenyl)-2-cyanoacetamide 1a-c as valuable synthons in the synthesis of simple active heterocyclic compounds and evaluate the resulted compounds as antimicrobial agents against strains of Escherichia coli (Gram negative bacteria) and Staphylococcus aureus (Gram positive bacteria) by the disc diffusion method [10,11] together with strains of fungi Aspergillus flavus and Candida albicans [12] by the agar diffusion method.…”

An Efficient Synthesis and Antibacterial Activity of Pyrido[2,3‐d]Pyrimidine, Chromeno[3,4‐c]Pyridine, Pyridine, Pyrimido[2,3‐c]Pyridazine, Enediamines, and Pyridazine Derivatives

“…In this repot a rapid one‐pot synthesis of enediamines with high yield and pure crystals by using arylazomalononitriles, whereas enediamines reported earlier after six separated successful steps . The present work aimed at synthesis of a variety of heterocycles using cyanoacetylurea (N‐carbamoyl‐2‐cyanoacetamide) 1 as starting materials , using new procedures for synthesis different heterocycles which have biological and medicinal activities.…”

Synthesis and antimicrobial activity of new hetrocycles obtained using cyanoacetylation

“…The activation of cyanoacetic acid by conversion to a mixed anhydride with acetic anhydride was also used [6 -8], but the generality, simplicity and usefulness of this method was not appreciated and this reagent was rarely used for N-acetylation of, e.g., urea and C-acetylations of enamines [9]. Other activation procedures, such as conversions to cyanoacetyl chloride, have also been used, although this reagent is characterized by a tendency to self-polymerization, particularly when heated [7].Recently, we reported the use of cyanoacetic acid in the synthesis of simple nitrogenated heterocyclic compounds [10,11] to demonstrate the general applicability of cyanoacetic acid -acetic anhydride reagent. We have investigated its scope on selected simple nitrogenated compounds, namely, 2-imidazolidone (Ia) and thiosemicarbazide (Ib) to afford 3-oxo-3-(2-oxoimidazol-1-yl)propanenitrile (IIa) and 2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide (IIb) respectively, in good yields (Scheme 1).…”

“…Recently, we reported the use of cyanoacetic acid in the synthesis of simple nitrogenated heterocyclic compounds [10,11] to demonstrate the general applicability of cyanoacetic acid -acetic anhydride reagent. We have investigated its scope on selected simple nitrogenated compounds, namely, 2-imidazolidone (Ia) and thiosemicarbazide (Ib) to afford 3-oxo-3-(2-oxoimidazol-1-yl)propanenitrile (IIa) and 2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide (IIb) respectively, in good yields (Scheme 1).…”