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The reaction of ethyl pyridine-2-ylcarbamate with phenacyl bromides in acetonitrile gave 2-aryl-1-(ethoxycarbonyl)-2-hydroxy-2-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridine-4-ium bromides which were con--verted into 2-arylimidazo[1,2-a]pyridines by heating in acetic anhydride, followed by treatment with potassium carbonate. [ABSTRACT FROM AUTHOR]

This article discusses the synthesis of (2 Z,5 Z)-3-benzyl/alkyl-5-(2-oxo-5-aryl-3 (2 H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones through a one-pot three-component reaction. Thiazolidine compounds have various applications in fields such as biological science and medicinal chemistry. The article presents a method for the synthesis of these compounds and discusses their potential biological features. The document provides information on the synthesis and characterization of various compounds, including their chemical structures, physical properties, and spectroscopic data. It is a valuable resource for researchers and scientists in the field of chemistry. [Extracted from the article]

In order to manufacture imidazo[1-b][1,3,4]thiadiazole, the beginning components that are used are the 2,4-dinitro benzoic acid and the thiosemicarbazide. The synthesis of the corresponding imidazolthadiazole derivative was brought about as a consequence of their interaction with phenacyl bromides, which are also referred to as p-substituted phenacyl bromides. The structure of these compounds was validated since the spectrum features of the compounds that were discussed before were taken into consideration. A couple of these compounds were shown to have an effect that varied from mild to moderate against the microorganisms Staphylococcus aureus, Candida albicans, Pseudomonas aeruginosa, and Escherichia coli. This was identified via the process of discovery. [ABSTRACT FROM AUTHOR]

We report a green and efficient method for the synthesis of 4-arylidene-1-(4-phenylselenazol-2-yl)-3-methyl-1H-pyrazole-5(4H)-ones from the condensation of phenacyl bromide, selenosemicarbazide with ethyl acetoacetate and aryl aldehyde in acetic acid using sodium acetate as a base. [ABSTRACT FROM AUTHOR]

Due to the increased interest in heterocyclic compounds over the past decade, many pharmaceutical and organic chemists have explored the synthesis of various materials. Among the many organic compounds that can be synthesized in a wide range of chemical reactions, phenacyl bromide has proven to be a good, inexpensive, versatile, and efficient intermediate. This review presents an overview of the significant applications of phenacyl bromide, focusing on its role in recent synthetic advances and its utility in multicomponent reactions and literature reports for 2017 to the end of 2021. [ABSTRACT FROM AUTHOR]

A number of new alkaloid-like phenylfuroacridones were synthesized by cyclization in polyphosphoric acid of 2-, 3 -, 4-(2-oxo-2-phenylethoxy)acridones, which, in turn, were obtained by O-alkylation of the corresponding 2-, 3-, 4-hydroxyacridones with phenacyl bromide. Biological studies showed that phenylfuroacridones exhibited a low antibacterial activity against the test strain Candida albicans. [ABSTRACT FROM AUTHOR]

A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide (3) in ethanol/water (1:1) gave 2-((5-(5-methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one (4) in a 76% yield. The structure of the title heterocycle (4) was confirmed by single-crystal X-ray diffraction and nuclear magnetic resonance. [ABSTRACT FROM AUTHOR]

A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide (3) in ethanol/water (1:1) gave 2-((5-(5-methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one (4) in a 76% yield. The structure of the title heterocycle (4) was confirmed by single-crystal X-ray diffraction and nuclear magnetic resonance.

The synthesis of step‐growth polymers by photoinduced methods is a challenging issue in synthetic chemistry. Here, we report a single component near UV responsive photopolymerization system for step‐growth polymerization of N‐methylpyrrole (MPyr) and N‐methylindole (MIn) by using phenacyl bromide (PAB). The obtained high molecular weight conjugated polymers were characterized by spectral and chromatographic methods. Detailed laser flash photolysis and spectroscopic studies revealed that polymerization proceeds by successive photoinduced cleavage of PAB followed by electron transfer, proton release and coupling processes. After photolysis, chain growth continues also in daylight or dark by acidic oxidation. The structural features of the polymers were investigated. PAB single component photoinitiator enables an efficient, rapid, room temperature step‐growth polymerization process of MPyr and MIn that can be applied to other conjugated monomers. [ABSTRACT FROM AUTHOR]

This study describes a fast and one-pot diastereoselective sequential three-component reaction (3CR) involving phenacyl bromide, malononitrile, and 4-oxo-4H-chromene-3-carbaldehyde. This reaction could be used for the preparation of highly functionalized 2-amino-4,5-dihydrofuran-3-crabonitrile. In this procedure, the desired product is obtained through a reaction of phenacylmalononitrile (obtained from the reaction of phenacyl bromide and malononitrile) with 4-oxochromene-3-carbaldehyde. This method has benefits such as good efficiency, proper diversity, relatively short reaction time, and simple product purification. A series of highly functionalized 2-amino-4,5-dihydrofuran-3-crabonitrile frameworks have been synthesized in excellent yields (80–85%) via a one-pot three-component reaction of phenacyl bromide, malononitrile, and 4-oxo-4H-chromene-3-carbaldehyde, in good yield. The value of this method lies in its short reaction time, convenient purification, no need for a metal catalyst, good efficiency, and green solvent. [ABSTRACT FROM AUTHOR]

• New methylthiourea-thiophene, -thiazole, or -pyrazole conjugates were synthesized and characterized. • DFT calculations disclosed that synthesized derivatives were nonplanar. • The resulted FMO's energies indicated that all the hybrids have little energy gap. • In-depth molecular docking was explored against the bacterial protein PDB ID 1AJ6. • Methylthiourea-conjugates may exhibit interaction owing to CYP450 isoform inhibition. A series of new functionalized thiophene, thiazole, and pyrazole conjugates with methylthiourea was synthesized by cyclization of 1-(4-(2-bromoacetyl)phenyl)-3-methylthiourea (1) with different thioacetanilides, aryl carbamodithioates, and hydrazonoyl cyanide reagents, respectively. The DFT/B3LYP method showed that the thiazole derivatives 5a–c had lower HOMO-LUMO energies and ΔE H-L than the thiophenes 3a–c and the pyrazoles 7a–c. The synthesized conjugates were examined to investigate their potential as antibacterial agents. Analogue 3a was found to be extremely effective against Gram-positive bacteria by rigorous biological screening, while analogues 3c and 7a were found to be effective against Gram-negative bacteria. Antifungal tests revealed that analogues 3c and 5b were very effective. Molecular docking studies of the bacterial protein PDB ID 1AJ6 showed that analogues 3b and 7b bind most strongly. This suggests that they have important interactions through hydrogen bonds and π-interactions that keep the ligand-receptor complex together. Interestingly, analogue 7b not only demonstrated the highest binding affinity but also excellent structural compatibility with the protein target, establishing it as a lead molecule for further investigation. Despite their promising pharmacological qualities, all analogues faced pharmacokinetic challenges such as poor gastrointestinal absorption and blood-brain barrier permeability. Analogue 3c , for instance, demonstrated a balance between lipophilicity and a lower Topological polar surface area (TPSA) value (113.49 Ų) that supports good gastrointestinal absorption while having poor projected bioavailability, according to Swiss-ADME. [ABSTRACT FROM AUTHOR]

Herein, a convenient and efficient synthesis of 7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives was achieved from the reaction of isoquinolinium N-ylides, aromatic aldehydes, and heterocyclic 1,3-dicarbonyl compounds via one-pot three-component diastereoselective domino reaction in good-to-excellent yields. The advantages of this protocol are easily available starting materials, operational simplicity, and avoidance of hazardous organic solvents and catalyst. The synthesized products were characterized by IR, 1H NMR, 13C NMR and mass spectra. Additionally, the conclusive structure of target compounds was confirmed by X-Ray diffraction analysis. [ABSTRACT FROM AUTHOR]

A series of new 2-(6H-indolo[2,3-b]quinoxalin-6-yl)-1-phenylethan-1-ones was synthesized by the reaction of various 6H-indolo[2,3-b]quinoxalines with 4-substituted 2-bromophenylethan-1-ones in a DMSO–K2CO3 system. [ABSTRACT FROM AUTHOR]

Several efficient, robust, versatile and straightforward strategies for the diversity-oriented convergent synthesis of a vast range of highly functionalized biologically active N-heterocycles such as quinoxaline, pyrazine, cyanopyrazine derivatives from different easily accessible, inexpensive starting motif has been reported by exploring the promising organo Cu (II) catalyst via double condensation/tandem oxidation-cyclization/elimination-cyclization reactions. These methodologies have several advantages such as inexpensive, non-toxic starting materials as well as catalyst and easy reaction set-up. Avoid the use of hazardous materials has added another important advantage in these protocols. [ABSTRACT FROM AUTHOR]

Ten new pyridine linked various substituted thiazole hybrids through (hydrazonomethyl)phenoxy-acetamide spacer were synthesized. The synthetic strategy was based on the reaction of the precursor 2-(4-((2-carbamothioylhydrazono)methyl)phenoxy)-N-(pyridin-2-yl)acetamide (3) with various α-halogenated carbonyl compounds (namely; phenacyl bromides, ethyl bromoacetate, diethyl bromomalonate and 3-chloropentane-2,4-dione). Moreover, the cytotoxicity properties of the synthesized compounds have been studied against liver carcinoma (HepG2), laryngeal carcinoma (Hep-2), prostate cancer (PC3), breast cancer (MCF-7) and normal fibroblast cells (WI38). The pyridine-thiazole compounds 7 and 10 revealed promising anticancer activity against MCF-7 and HepG2 cell lines with IC50 values in the range 5.36–8.76 μM compared to the activity of 5-fluorouracil. Docking study provided valuable insights for binding sites of the synthesized compounds with Rho-associated protein kinase (ROCK-1).

Hydrazinyl thiazole is frequently encountered in natural as well as in synthetic compounds. It is also an important pharmacophore and has some other useful applications. In this review article, we have compiled different green synthetic procedures for the synthesis of hydrazinyl thiazole derivatives. Also, the critical analysis of different synthetic schemes will help to understand the lacks in developed procedures and to develop new methodologies regarding its synthesis, specially using heterogeneous organocatalyst and photocatalyst. [ABSTRACT FROM AUTHOR]

Discovery towards the potent antimicrobial agents is indispensable for the treatment of infections caused by resistant microbes. Thus, we prepared a novel series of 3-substituted 5-phenylindeno-thiazolopyrimidinone derivatives following conventional method. All the molecules were investigated for their in vitro antimicrobial potency against different bacteria and fungi, and the results were compared with streptomycin and clotrimazole standard drugs, respectively. Among the twelve analogs, 4-methoxyphenyl-5-phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-one showed equipotent activity against a bacterium, Staphylococcus aureus (minimum inhibitory concentration 25 µg/mL and zone of inhibition 22 mm), and a fungus, Aspergillus niger (zone of inhibition 20 mm). The rest of the thiazolo[3,2-a]pyrimidin-6(5H)-one derivatives exhibited week to reasonable activities against the tested bacterial and fungal strains. [ABSTRACT FROM AUTHOR]

Abstract Background Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. Results 4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)-N′-phenylpropane hydrazonoyl chlorides 5a–c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a–c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC50 = 1.61 ± 1.92 (μg/mL)) and 11 (IC50 = 1.98 ± 1.22 (μg/mL)). The structure–activity relationships have been suggested based on their anticancer results. Conclusions A novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents.

A facile protocol for the synthesis of 2-arylimidazo [1,2-a]pyridines was developed using two-component cyclization of substituted 2-aminopyridines and substituted phenacyl bromides in 65-94% yield. The reaction was DBU catalysed using green solvent, aqueous ethanol (1 : 1 v/v) at room temperature. The atom economy of the products was calculated to be 66.25-73.41%. The developed protocol successfully exhibits a broad substrate scope, less reaction time, high to moderate yield and multigram scale synthesis. [ABSTRACT FROM AUTHOR]

A general and efficient method has been developed for the synthesis of NH-indoles bearing electron-accepting substituents via the modification of corresponding N-hydroxyindoles. [ABSTRACT FROM AUTHOR]

In this study, a series of highly stereoselective polysubstituted cyclopropane derivatives (trans‐2,3‐dihydro‐spiro[2‐aroyl‐3‐aryl‐cyclopropane]1,2‐indene‐1,3‐diones) were synthesized via a one‐pot two‐step tandem reaction starting from phenacyl bromide derivatives, 1,3‐indanedione and aromatic aldehydes in ethanol using 1,4‐diazabicyclo[2.2.2]octane (DABCO) as a co‐catalyst and Fe3O4\SiO2\propyltriethoxysilane\L‐proline as a nanomagnetic organocatalyst. This synthesized nanocatalyst was characterized by Fourier transforms infrared (FT‐IR) spectroscopy, energy dispersive X‐ray (EDX) analysis and scanning electron microscopy (SEM) images to confirm the formation of the nanocomposite. The catalyst can be easily recovered by simple magnetic decantation and their catalytic activity remains unaltered after ten consecutive cycles, making them environmentally‐friendly and widely applicable due to their efficiency, ease of handling and cost effectiveness. Stereoselective polysubstituted cyclopropane: A series of highly stereoselective polysubstituted cyclopropane derivatives, trans‐2,3‐dihydrospiro[2‐aroyl‐3‐aryl‐cyclopropane]1,3‐indanedione were synthesized via one‐pot two‐step tandem reaction starting from phenacyl bromide derivatives, 1,3‐indanedione and aromatic aldehydes in ethanol using DABCO as a co‐catalyst and Fe3O4\SiO2\propyltriethoxysilane\L‐proline as a nanomagnetic organocatalyst. This synthesized nanocatalyst was characterized by SEM, FT‐IR, EDX analyses to confirm the formation of the nanocomposite. [ABSTRACT FROM AUTHOR]

An efficient synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5-amines was accomplished by a simple, atom-economical, and multicomponent approach. Reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol with various phenacyl bromides and benzoylacetonitriles in ethanol and catalytic amount of acetic acid afforded the titled compounds. The structures of newly synthesized compounds were confirmed by their analytical and spectral (IR, ¹H-NMR, 13C-NMR, and Mass) data. [ABSTRACT FROM AUTHOR]

A facile microwave assisted reaction of phenacyl bromide and 2-amino pyridine is catalyzed by Nano SiO2 under solvent free conditions to give corresponding Imidazo[1,2- a]pyridines in good yields. Reactions proceed with high efficiency and good functional group tolerance. This approach provides a useful protocol for the preparation of highly substituted Imidazo[1,2-a]pyridine derivatives. [ABSTRACT FROM AUTHOR]

Abstract: An efficient, mild, and convenient protocol for the synthesis of aryl(thieno[2,3-b]quinolin-2-yl)methanone and 2-(2-aroyl-2,3-dihydrothieno[2,3-b]quinolin-3-yl)-1-arylethanone derivatives from readily available starting materials via a sequential multi-component reaction has been developed. The products were obtained with excellent yield (85-95%) within short reaction times (25-30 min) in DMF at room temperature. The structures of all synthesized compounds were characterized using IR, 1H NMR, 13C NMR, and mass spectral data and elemental analysis.Graphical abstract: [ABSTRACT FROM AUTHOR]

The solid-solid reactions of thiosemicarbazide with 4-formylantipyrine, 2-acetylpyrrole and camphor were performed to afford the thiosemicarbazones 1–3 which underwent hetero-cyclization with phenacyl bromide to furnish the corresponding thiazole derivatives 4–6. The yields of the reactions are quantitative in all cases and the products do not require further purification. A series of 5-arylazo-2-(substituted ylidene-hydrazinyl)-thiazole dyes 7–9 was then prepared by diazo coupling of thiazole derivatives 4–6 with several diazonium chlorides. The synthesized dyes were applied as disperse dyes for dyeing polyester fabric. The dyed fabrics exhibit good washing, perspiration, sublimation and light fastness properties, with little variation in their moderate to good rubbing fastness.

An efficient synthesis of 6-(2-chloro-4-fluorophenyl)-9-phenylimidazo[1,2-a][1,8]naphthyridine derivatives by the reaction of phenacyl bromide with substituted heterocyclic amines in the presence of DABCO catalyst is described. Solid state conditions of the process accelerate accumulation of the targeted products with high yields and exclude formation of side-products. Antibacterial and fungal activities tests of all newly synthesized products demonstrate their pronounced potency, which is the highest for compounds 5c-5e. Molecular docking studies support well with the antimicrobial activity data accumulated for the products. [ABSTRACT FROM AUTHOR]

A greener approach for the synthesis of 4-oxo-4,5,6,7-tetrahydro indole derivatives has been achieved through Wang-OSO3H-mediated three-component reaction involving dimedone, phenacyl bromide, and primary amine in water. A variety of indole derivatives were prepared using this operationally simple and straight forward methodology in acceptable yields. [ABSTRACT FROM AUTHOR]

Abstract: A new approach to the synthesis of new heterocyclic compounds with benzoylisothiocyanate, amines, and 2‐bromoacetophenone (phenacyl bromide) fragments in one molecule has been developed. The synthesis method comprises condensation reaction for the preparation of novel (4‐phenylthiazol‐2(3H)‐ylidene) benzamide derivatives. These new compounds were synthesized via one‐pot and multicomponent reaction of 2‐furanmethylamine, 5‐chloro‐2‐phenoxyaniline, and 1‐naphthylamine with phenacyl bromide and substituted benzoylisothiocyanates. Moreover, new series of anthraquinone‐thiazole hybrids have been synthesized. These compounds were prepared from unsymmetrical thiourea containing anthraquinone and dialkyl acetylenedicarboxylate. The nature of the compounds was confirmed by IR, 1HNMR, 13CNMR, mass spectrometry, and CHNS elemental analysis. The structural elucidation was accomplished by single‐crystal X‐ray diffraction methods. [ABSTRACT FROM AUTHOR]

Background: Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. Results: 4-Methyl-2-phenylthiazole-5-carbohydrazide ( 2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)- N-phenylhydrazinecarbothioamide ( 3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)- N′-phenylpropane hydrazonoyl chlorides 5a- c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a- c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione ( 8) or 2-chloro-3-oxo- N-phenyl butanamide ( 10) phenacyl bromide 12 ethyl chloroacetate ( 14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC = 1.61 ± 1.92 (μg/mL)) and 11 (IC = 1.98 ± 1.22 (μg/mL)). The structure-activity relationships have been suggested based on their anticancer results. Conclusions: A novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents. [ABSTRACT FROM AUTHOR]

Synthesis of [3,4-b][1,3,4]thiadiazines from the condensation of 4-amino-6-methyl-3-thioxo-1,2,4-triazine-5(2H)-one (AMTTO) or 4-amino-1,4-dihydro-5-methyle-1,2,4-triazole-5-thione (AMTT) with phenacyl bromide in the presence of a catalytic amount of various heteropolyacids (HPAs) under refluxing conditions is reported. DOI: http://dx.doi.org/10.4314/bcse.v28i1.8

Various imidazolo[1,2-a]pyridines were synthesized from amino pyridines and aromatic phenacyl bromides by one step process in the presence of MgO in aqueous medium at room temperature. The salient feature of this method includes mild conditions, short reaction time, high yields, easy purification and simple procedure.

The aim of this study was to synthesize imidazo[2,1- b][1,3,4]thiadiazole derivatives, characterize them with various spectroscopic methods and investigate their antifungal activities. 2-Αmino-1,3,4-thiadiazole derivatives 2a, b were synthesized by reacting nitrile compounds 1a, b with thiosemicarbazide (yields 75 and 88%). We then synthesized imidazo[2,1- b][1,3,4]thiadiazole derivatives 4-21, the target compounds, from the reactions of 2-amino-1,3,4-thiadiazole derivatives 2a, b with phenacyl bromide derivatives 3 (yields 52-69%). The structures of all synthesized compounds were characterized by infrared, H nuclear magnetic resonance, C nuclear magnetic resonance, elemental analysis and mass spectroscopy and X-ray diffraction analysis was also used for the compounds 7, 8, 10, and 17. Subsequently, in vitro antifungal activity tests were applied to all synthesized compounds. Inhibition zones, percentages of inhibition and LD50 doses were determined. Most of the synthesized compounds exhibited good antifungal activity against plant pathogens. Molecular docking and electronic properties calculations were carried out in order to see the potential binding conformations of the ligands and the effect of the substituents on the activities. Docking score successfully reflects the activity of the most active compound 10, which was found to have the lowest octanol/water partition coefficient and high HOMO energy value. The combination of experimental and computational work show that all the synthesized compounds have promising activities and might serve as novel drug candidates. [ABSTRACT FROM AUTHOR]