57626-33-2

Upstream product

• 93-91-4 1-phenylbutan-1,3-dione 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 56570-63-9 ((E)-3-(dimethylamino)-1-phenylbut-2-en-1-one) 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 97467-19-1 2,2-dibromo-1-phenylbutane-1,3-dione 

Downstream Products

• 57626-42-3 (6-methyl-imidazo[2,1-b]thiazol-5-yl)-phenyl-methanone 
• 114171-31-2 5-acetyl-2-(hexahydroazepin-1-yl)-4-phenylthiazole 
• 114171-30-1 5-benzoyl-2-(hexahydroazepin-1-yl)-4-methylthiazole 
• 93832-52-1 5-benzoyl-4-methyl-2-(N-methyl-N-phenylamino)thiazole 
• 111753-03-8 1-{2-[N-methyl(phenyl)amino]-4-phenyl-1,3-thiazol-5-yl}ethanone 
• 51439-47-5 1,2-diacetyl-1,2-dibenzoylethane 
• 16883-69-5 N-phenacylpyridinium bromide 
• 61122-83-6 1-phenyl-1-(2-methylimidazo[1,2-a]pyridin-3-yl)methanone 
• 243456-06-6 3,5-bis-(4-bromophenyl)-[1,2,4]thiadiazole 
• 4115-18-8 3,5-bis-(4-methoxyphenyl)-[1,2,4]thiadiazole 
• 70540-36-2 3,5-bis(2-chlorophenyl)[1,2,4]thiadiazole  
• 17590-34-0 3,5-di-p-tolyl-[1,2,4]thiadiazole 
• 86814-28-0 3,5-bis(4-nitrophenyl)-1,2,4-thiadiazole 
• 70650-90-7 3,5-bis-(3-chlorophenyl)-[1,2,4]thiadiazole 

Relevant academic research and scientific papers

CF3S(O)n-Containing olefins in cyclopropanation reactions

Cyclopropanation of trifluoromethyl(sulfinyl, sulfonyl) ethylenes was achieved by utilization of α-bromo- or α,α-dibromo 1,3-dicarbonyl compounds in the presence of bases. DBU was found to be the best choice to get satisfactory yields of cyclopropanes with CF3S(O)n (n = 1, 2) groups if α-bromo-1,3-dicarbonyl compounds were used. A series of new cyclopropanes bearing trifluoromethylsulfinyl group were synthesized.

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

Lipophilic indole mediated chemoselective α-monobromination of 1,3-dicarbonyl compounds

A mild and efficient mono-selective bromination of 1,3-dicarbonyl compounds has been developed using lipophilic indole catalysts. Inexpensive and commercially available N-bromosuccinimide (NBS) was used as the brominating reagent. The selectivity was further enhanced when using stoichiometric amount of 3-bromoindole species. Mechanistic studies reveal that the indole catalyst has dual functions in the mono-bromination process.

Copper nitrate-catalyzed α -bromination of aryl ketones with hydrobromic acid

An efficient method for α-bromination of aryl ketones, using the combination of molecular oxygen and aqueous hydrobromic acid as a brominating agent in the presence of the copper nitrate, has been developed. This catalytic system, which uses cheap and readily available reactants, shows good atom economy with water as the only by-product.

A quick, mild and efficient bromination using a CFBSA/KBr system

Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.

NBS mediated one-pot regioselective synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines and their unambiguous characterization through 2D NMR and X-ray crystallography

A simple and mild protocol towards the regioselective synthesis of 1-aryl/heteroaryl-1-(2-methylimidazo[1,2-a]pyridin-3-yl)methanones has been developed by one-pot condensation of 2-aminopyridine with 1,3-diketones involving the intermediacy of 2-bromo-1,

TsNBr2mediated oxidative functionalization of alkynes

A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2mediated process. Alkynes could be readily converted to ketones and α-bromoketones via an oxybromination–debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2and Na2SO3in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding α-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2at room temperature. In all cases, excellent yields of corresponding products are obtained.

Vanadium (V) oxide mediated bromolactonization of alkenoic acids

A full account of our recently communicated method for the V2O5 mediated bromolactonization of alkenoic acids is presented. Here we describe the extensive evaluation of the metal oxide catalyst, terminal oxidant, halide source, solvent system, and reaction temperature that resulted in optimal conditions employing 0.05 equiv V2O5, 3 equiv urea-hydrogen peroxide complex (UHP), and 3 equiv of NH4Br in an acetone:H2O (6:1) solvent system at room temperature. Additionally, we have expanded the substrate scope of the reaction with the aim of evaluating the functional group tolerance of the transformation. Further, we present preliminary data of a related halogenation of β-diketones with our optimal conditions. Finally, we probed the role of urea in the transformation.

Novel Metal- and Mineral-Acid-Free Synthesis of Organic Ammonium Tribromides and Application of Ethylenephenanthrolium Bistribromide for Bromination of Active Methylene Group of 1,3-Diketones and β-Ketoesters

A novel procedure for the preparation of organic ammonium tribromides (OATBs) is described from their corresponding bromides. Quaternary ammonium bromides (QABs) and a N,N′-heterocyclic dibromide are efficiently oxidized to their corresponding monotribromides and bistribromide by m-chloroperbenzoic acid (MCPBA) in the presence of 2 and 4 equiv of KBr, respectively. The reactions are carried out in an aqueous medium without the use of any mineral acid or metal catalyst/promoters. A variety of tribromides are synthesized in very good yields including a hitherto unknown reagent, 1,10-(ethane-1, 2-diyl)phenanthrolinediium bistribromide (EPDBT). EPDBT is investigated as brominating agent and found to be highly effective for selective bromination of active methylene groups of a variety of 1,3-diketones and β-ketoesters. GRAPHICAL ABSTRACT.

Metal-free protocol for the synthesis of α-bromo ketones from olefins using TsNBr2

TsNBr2 reacts readily with olefins to produce α-bromo ketones at room temperature. The synthesis was carried out by treating an olefin with TsNBr2 in acetone-water mixture in 30:1 ratio. Excellent yield of corresponding α-bromo ketone could be achieved within a short time.