175714-45-1Relevant articles and documents
Simple and efficient protocol for the synthesis of benzoxazole, benzoimidazole and benzothiazole heterocycles using Fe(III)–Schiff base/SBA-15 as a nanocatalyst
Bardajee, Ghasem Rezanejade,Mohammadi, Marzieh,Yari, Hasan,Ghaedi, Aseyeh
, p. 265 - 270 (2016)
Benzimidazoles, benzoxazoles, and benzothiazoles derivatives were synthesized from condensation of aldehydes and 1,2-phenylenediamine or ortho-aminophenol or ortho-aminothiophenol in the presence of catalytic amount of Fe(III)–Schiff base/SBA-15 in water
Iron(III)–salen complex on a polymer scaffold as heterogeneous catalyst for synthesis of benzimidazoles
Balinge, Kamlesh Rudreshwar,Datir, Sagar Krushnarao,Khajone, Vijay Baburao,Bhansali, Karan Jivanlal,Khiratkar, Avinash Ganesh,Bhagat, Pundlik Rambhau
, p. 155 - 168 (2019)
Benzimidazoles are important bioactive compounds with diverse applications in the medicinal, industrial, as well as agrochemical fields. In this study, an iron–salen complex on a polymer scaffold was synthesized and characterized, and its performance asse
Novel Mcl-1/Bcl-2 dual inhibitors created by the structure-based hybridization of drug-divided building blocks and a fragment deconstructed from a known two-face BH3 mimetic
Zhang, Zhichao,Su, Pengchen,Li, Xiangqian,Song, Ting,Chai, Gaobo,Yu, Xiaoyan,Zhang, Keren
, p. 89 - 99 (2015)
We have previously reported a small-molecule two-face Bim BH3 mimetic, 2,3-dihydroxy-6-(4-isopropylphenylthio)anthracene-9,10-dione (1). Herein, we linked a polyphenol fragment, which was deconstructed from compound 1, with a drug-derived building block g
An Unexpected Formation of 2-Arylbenzimidazoles from α,α-Diiodo-α’-acetoxyketones and o-Phenylenediamines
Sadhukhan, Santu,Mondal, Swagata,Baire, Beeraiah
, (2022/03/01)
An unusual reactivity of the α,α-diiodo-α’-acetoxyketones with o-phenylenediamines is reported through the formation of 2-arylbenzimidazoles. A systematic study through a series of fruitful control experiments and isolation of key intermediates unravelled the unprecedented domino mechanism. This process involves a stepwise two-carbon fragmentation pathway through domino and sequential amidation–aziridination–decarbonylation–I2-mediated aminative cyclization–oxidation reactions. This strategy employs no additives like oxidant, metal catalyst, bases, and represents yet another novel reactivity profile of the building blocks α,α-diiodo-α’-acetoxyketones.
One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles
Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao
supporting information, (2022/02/07)
It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.
Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
, p. 6705 - 6716 (2021/12/31)
We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.
A facile and efficient synthesis of benzimidazole as potential anticancer agents
Hoang, Thi-Kim-Dung,Huynh, Thi-Kim-Chi,Nguyen, Thanh-Danh,Nguyen, Thi-Hong-An,Tran, Ngoc-Hoang-Son
, (2020/07/13)
Abstract: This study reports a simple process to synthesize and separate of 2-(substituted-phenyl) benzimidazole derivatives with high yield and efficiency. Specifically, by reacting ortho-phenylenediamines with benzaldehydes using sodium metabisulphite a
An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
Ibrahim, Tarek S.,Seliem, Israa A.,Panda, Siva S.,Al-Mahmoudy, Amany M.M.,Abdel-Samii, Zakaria K.M.,Alhakamy, Nabil A.,Asfour, Hani Z.,Elagawany, Mohamed
, (2020/06/17)
A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.
A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
Maphupha, Mudzuli,Juma, Wanyama P.,De Koning, Charles B.,Brady, Dean
, p. 39496 - 39510 (2018/12/13)
Heterocyclic aromatic compounds containing an imine (C═N) bond such as benzimidazoles and benzothiazoles are important active pharmaceutical ingredients. The synthesis of 2-aryl-1H-benzimidazoles and 2-arylbenzothiazoles in good to excellent yields was ac
Preparation of 2-Arylbenzimidazole derivatives using CuO nanoparticles /H2O2 system
Fazlinia, Abbas,Sheikh, Setareh
, p. 126 - 130 (2018/02/06)
CuO nanoparticles were prepared in watery lemon juice media and were characterized by XRD, FE-SEM, DLS, TGA and BET analysis. The as-prepared catalyst was efficient and recyclable for a high yielding, and practical method for the synthesis of 2-arylbenzimidazoles via cyclo-condensation reaction of 1,2-benzenediamine and aldehydes using copper oxide (CuO) nanoparticles is reported. Solvents and solvent-free effects on the reaction were investigated. Solvent plays a significant role in the reaction, and best results were achieved in solvent-free condition at 80°C. All reactions were completed in short reaction times (20–120?min) with 76–97% yields.
