6595-23-9Relevant academic research and scientific papers
Highly effective procedure for introduction of amino group into the 2-position of imidazole ring
Kawasaki, Ikuo,Taguchi, Norio,Yoneda, Youko,Yamashita, Masayuki,Ohta, Shunsaku
, p. 1375 - 1379 (2007/10/03)
Procedures for the preparation of 2-amino- and 2-arylaminobenzimidazoles were developed, and one of the efficient procedure was applied to the synthesis of preclathridine A, a marine imidazole alkaloid isolated from a sponge.
Conformational Properties of the Free and Methylated 2-Amino Group in Benzimidazole, Benzoxazole, and Benzothiazole. X-Ray Crystallographic Analysis and Nuclear Magnetic Resonance Study of the Internal Rotation
Benassi, Rois,Grandi, Romano,Pagnoni, Ugo M.,Taddei, Ferdinando,Bocelli, Gabriele,Sgarabotto, Paolo
, p. 1513 - 1522 (2007/10/02)
The conformational properties of the free and methylated 2-amino group in benzimidazole, 1-methylbenzimidazole, benzo-oxazole, and benzothiazole were studied, as well as the modifications induced by N-protonation and N-methylation at the heterocyclic ring.Both 1H n.m.r. spectra and X-ray analysis show that in the ground state of the molecules examined the amino group is coplanar with respect to the plane of the rings.The NN-dimethylamino group tends to be distorted from coplanarity when a methyl group is present at the heterocyclic nitrogen: the degree of distortion determined experimentally compares satisfactorily with that corresponding to the energy minimum of the molecules calculated by semi-empirical methods.For the benzoxazole and benzothiazole derivatives it was also possible through 1H dynamic n.m.r. measurements to determine the thermodynamic parameters for the internal rotation of the NN-dimethylamino group; and in the N-protonated forms the free energy of activation turns out to be higher than that in the free bases.
The Copper-Catalysed Reaction of 2-Chloroimidazoles and 2-Chlorobenzimidazoles with Dimethylamine
Whittle, Chrostopher P.
, p. 1545 - 1551 (2007/10/02)
The preparation of 2-dimethylamino-benzimidazoles and -imidazoles from the corresponding 2-chloro compounds by reaction with dimethylamine is assisted by the presence of copper salts.In the absence of a copper catalyst, 2-chloroimidazoles fail to react.Ki
