43154-48-9Relevant academic research and scientific papers
Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement
Zhang, Xiaohui,Huang, Ruofeng,Marrot, Jér?me,Coeffard, Vincent,Xiong, Yan
, p. 700 - 708 (2015/02/02)
A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.
Iodobenzene catalyzed C-H amination of N-substituted amidines using m-chloroperbenzoic acid
Alla, Santhosh Kumar,Kumar, Rapolu Kiran,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
supporting information, p. 1334 - 1337 (2013/04/23)
The oxidative C-H amination of N″-aryl-N′-tosyl/N′- methylsulfonylamidines and N,N′-bis(aryl)amidines has been accomplished using iodobenzene as a catalyst to furnish 1,2-disubstituted benzimidazoles in the presence of mCPBA as a terminal oxidant at room temperature. The reaction is general, and the target products can be obtained in moderate to high yields.
