28291-75-0Relevant articles and documents
Molecular iodine-mediated synthesis of thiocarbamates from thiols, isocyanides and water under metal-free conditions
Bao, Wen-Hu,Wu, Chao,Wang, Jing-Ting,Xia, Wen,Chen, Ping,Tang, Zilong,Xu, Xinhua,He, Wei-Min
supporting information, p. 7025 - 7029 (2018/10/02)
A simple and practical molecular iodine-mediated method for the efficient construction of thiocarbamates from isocyanides, thiols and water under metal-free and mild conditions has been developed. A variety of thiocarbamates were easily synthesized through this methodology, which has the advantages of simple operation, eco-friendly conditions, good functional group tolerance, and readily accessible raw materials.
Iodine-catalyzed formation of substituted 2-aminobenzothiazole derivatives in PEG400
Dumonteil,Hiebel,Scherrmann,Berteina-Raboin
, p. 73517 - 73521 (2016/08/19)
An iodine-catalyzed formation of substituted 2-aminobenzothiazole derivatives is herein described using hydrogen peroxide as an oxidant in PEG400. The method enabled an efficient environmentally sound access to this valuable scaffold in moderate to excellent yields under metal-free conditions.
A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids
Chen, Ling,Huang, Bin,Nie, Quan,Cai, Mingzhong
, p. 446 - 450 (2016/05/19)
A copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates was achieved in hydrophobic [bmim][PF6] ionic liquid under mild conditions, generating a variety of 2-aminobenzothiazoles in good to excellent yields. The tandem reaction that was carried out in [bmim][PF6] has some obvious advantages such as accelerated reaction rate and increased yield as compared with the reaction run in volatile solvents such as toluene. Furthermore, the CuI/1,10-phenanthroline catalytic system can be reused up to eight times without loss of activity and efficiency.
A Synthesis of Benzothiazoles and Indoles by Direct C(sp2)-I Activation Catalyzed by Copper(II) on Silica-Coated Magnetite Nanoparticles
Moghadam, Faeze Kiani,Jarrah, Najmeh,Mashayekh-Salehi, Ali,Ghanbaripour, Rashid
, p. 1665 - 1668 (2016/07/06)
N-Substituted 2-amino-1,3-benzothiazoles and 2,3-disubstituted indoles were prepared by C-S and C-C cross-coupling reactions of 2-iodoanilines with isothiocyanates or 1,3-dicarbonyl compounds, respectively, in the presence of magnetic nanoparticles functionalized with a copper(II)-Schiff base complex as an efficient and reusable catalyst.
Water-Mediated Synthesis of Benzazole and Thiourea Motifs by Reacting Naturally Occurring Isothiocyanate with Amines
Sharma, Ritika,Bala, Manju,Verma, Praveen Kumar,Singh, Bikram
supporting information, p. 2106 - 2114 (2015/09/01)
An efficient, green, and facile method has been developed for the synthesis of benzazole and thiourea analogues from naturally occurring erucin in moderate to good yields. The reaction was carried out in water without using any metal catalyst or base. The present method tolerated the various functional groups on aromatic rings and also applicable for other isothiocyanates.
Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide
Zeng, Weilan,Dang, Pan,Zhang, Xiaoyun,Liang, Yun,Peng, Caiyun
, p. 31003 - 31006 (2014/08/05)
An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles has been developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(ii) trifluoromethanesulfonate to afford the corresponding 2-aminobenzothiazole derivatives in good to perfect yields. This journal is the Partner Organisations 2014.
Copper/N,N,N',N'-tetramethylethylenediamine-catalyzed synthesis of N-substituted benzoheterocycles via C-S cross-coupling at ambient temperature in water
Zhao, Na,Liu, Liang,Wang, Fei,Li, Jia,Zhang, Wu
supporting information, p. 2575 - 2579 (2014/09/17)
Copper/N,N,N',N'-tetramethylethylenediamine (Cu/TMEDA)-catalyzed ambient temperature tandem reactions of isothiocyanates with 2-iodophenols or 2-iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2-iminobenzo-1, 3- oxathioles and 2-aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (1mol%) and can yield the products on a gram scale.
Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles
Toulot, Stephanie,Heinrich, Timo,Leroux, Frederic R.
supporting information, p. 3263 - 3272 (2013/12/04)
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
Sousa, Ana Catarina,Martins, Lígia O.,Robalo, M. Paula
supporting information, p. 2908 - 2917 (2014/03/21)
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.
Cobalt-catalyzed oxidative isocyanide insertion to amine-based bisnucleophiles: Diverse synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles
Zhu, Tong-Hao,Wang, Shun-Yi,Wang, Gao-Nan,Ji, Shun-Jun
supporting information, p. 5850 - 5853 (2013/06/26)
Cobalt catalysis: Synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles was achieved by using cobalt(II) acetate catalyzed isocyanide insertion to o-diaminobenzene, 2-aminobenzenethiol, and 2-aminophenol derivatives in 1,4-dioxane (see scheme). It was found that the reaction proceeded efficiently to give the desired products in up to 95 % isolated yields by C-N and C-S (O, N) formation in a single step. Copyright