39235-96-6Relevant articles and documents
Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach
Chakraborty, Gargi,Guin, Amit Kumar,Mondal, Rakesh,Paul, Nanda
, p. 7217 - 7233 (2021/08/30)
Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.
Synthesis of 1,2-disubstituted benzimidazoles through DDQ-oxidized intramolecular dehydrogenative coupling of N,N′-dialkyl o-phenylenediamines
Feng, Yangyang,Ma, Youcai,Xiong, Ruimei,Xiong, Yan,Zhang, Xiaohui
, (2020/09/02)
The synthetic methodology of 1,2-disubstituted benzimidazoles has been developed, which starts from N,N′-dialkyl o-phenylenediamines via intramolecular dehydrogenative coupling under the oxidation of DDQ with mild conditions. Through detailed optimization of reaction conditions, only DDQ was found essential without any additives to reach to the highest yield of 99%. In the cases of linear aliphatic substituents, the synthesis of 1-alkyl-2-phenylbenzimidazoles showed high selectivities and their structures were identified by 2D NMR COSY correlation analysis. A plausible mechanism was proposed to interpret the observed reactivities and selectivities.
Bimetallic Cu-Mn B spinel oxide catalyzed oxidative synthesis of 1,2-disubstituted benzimidazoles from benzyl bromides
Sharma, Rohit,Sofi, Firdoos Ahmad,Rana, Preeti,Bharatam, Prasad V.
supporting information, p. 4013 - 4016 (2019/03/08)
Cu-Mn B (a heterogeneous catalyst) catalyzed synthesis of 1-benzyl-2-phenyl-1H-benzo[d]imidazoles is reported. In this reaction, 2-phenyl-1H-benzo[d]imidazoles are found to be the side products. The reported protocol is simple and highly efficient, tolerates a wide variety of substrates and the products were formed in good to excellent yield.