81093-59-6

Upstream product

• 616-45-5 2-pyrrolidinon 
• 95-16-9 1,3-Benzothiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 1123-99-5 2-iodobenzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 81093-55-2 2-(4-Chlorbutyrylamino)-benzthiazol 

Relevant academic research and scientific papers

Synthesis of N -Aryl and N -Heteroaryl γ-, δ-, and ?-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof

Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl 2 ·TMEDA (M = Zn or Cd; TMEDA = N, N, N ′, N ′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N -arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.

Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key molecules in pharmaceutical research. Copyright

Laccase-catalysed homocoupling of primary aromatic amines towards the biosynthesis of dyes

Coloured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p-electron donor pri-mary aromatic amines using two different laccases, CotA-laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange-red to purple products, presenting high molar extinction coeffi-cients, presumably result from oxidative homocou-pling reactions, through the formation of N-C bonds at positions 2 and 5, of the laccase oxidised inter-mediate as showed in the proposed oxidative path-way. The product of 1,4-phenylenediamine is shown to be the trimer known as Bandrowski's base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p-electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data con-tribute for (i) understanding key features of laccase reactivity with p-substituted aromatic amines and (ii) establishing enzymatic processes that lead to the syn-thesis of coloured bio-products under mild condi-tions with potential impact in the cosmetic and dye industries.

Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes

CH, NH coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)2 and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)2-2PPh3 and 4 equiv of NaOAc under O2 or in the presence of Ag2CO3 under N 2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended π-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag 2CO3 as an additive and Cu(OAc)2-2PPh 3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo CH, NH amidation.

Copper-mediated amidation of heterocyclic and aromatic C-H bonds

A copper-mediated aerobic coupling reaction enables direct amidation of heterocycles or aromatics having weakly acidic C-H bonds with a variety of nitrogen nucleophiles. These reactions provide efficient access to many biologically important skeletons, in

Syntheses of Some 2-Pyrrolidones Carrying N-Heterocycles as Substituents

Cyclisations of 2-(4-chlorobutyrylamino)thiazoles or 2,5-bis(4-chlorobutyrylamino)-1,3,4-thiadiazole in the presence of piperidine or ammonia lead to 1--2-pyrrolidones and 2,5-bis(2-oxopyrrolidino)-1,3,4-thiadiazole, in analogy to the synthes