56048-77-2Relevant articles and documents
An efficient and environmental benign synthesis of 2-benzimidazoles and 2-benzothiazoles using CeCl3-NaI as catalyst
Zhu, Xun,Wei, Yunyang
, p. 119 - 121 (2013/04/23)
A one-pot condensation of an aldehyde with 1,2-phenylenediamine or 2-aminothiophenol in dimethyl carbonate at 100°C under O2 in the presence of catalytic amounts of CeCl3-NaI gave an imine intermediate, which cyclised and dehydrogenated to give 2-arylbenzimidazoles or 2-arylbenzothiazoles in good yields.
Chiral phosphoric acid catalyzed transfer hydrogenation: Facile synthetic access to highly optically active trifluoromethylated amines
Henseler, Alexander,Kato, Masanori,Mori, Keiji,Akiyama, Takahiko
supporting information; experimental part, p. 8180 - 8183 (2011/10/09)
Amines to an end: Highly optically active α-CF3- functionalized amines can be obtained using metal-free reaction conditions. The method involves the transfer hydrogenation of CF3-substituted ketimines catalyzed by 1 and reductive ami
Lewis Acid-prompted Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds by 2-Phenylbenzothiazoline (2-Phenyl-2,3-dihydrobenzothiazole)
Chikashita, Hidenori,Miyazaki, Makoto,Itoh, Kazuyoshi
, p. 699 - 706 (2007/10/02)
Reduction of various α,β-unsaturated ketones (3a-g) and (4a-d) in methanol by the benzothiazoline (1) in the presence of aluminium chloride gives, in all cases, the corresponding saturated ketones (5a-g) and (6a-d)without any of the unsaturated or saturated alcohol.Reduction of α,β-unsaturated esters (7a,b) similarly gives the saturated esters (9a,b), while reaction of cinnamaldehyde (8) with compound (1) does not occur at all.Among the Lewis acids examined, aluminium chloride gives the best results.Reduction of 2'-azachalcone (21) with 2-phenylbenzothiazoline reveals that, in the reduction product, the deuterium atom is located at the β-position with respect to the carbonyl group.The result obtained from the reduction of the same substrate with compound (1) in methanol shows that no incorporation of a hydrogen atom from the solvent takes place and suggests (indirectly) that the introduced hydrogen atom at the α-position of the product comes from the benzothiazoline (1).The reaction of (Z)-1,2-dibenzoyl-1,2-diphenylethylene (30) with compound (1) in the presence of aluminium chloride stereospecifically yields meso-1,2-dibenzoyl-1,2-diphenylethane (31).This shows that the transfer of two hydrogens from compound (1) to the carbon-carbon double bond of the enone proceeds via cis-addition.Experiments with ethyl phenylpropiolate (28) also support cis-reduction for the present conjugate reduction.These results are interpreted in terms of a mechanism involving synchronous transport of a pair of hydrogens from the benzothiazoline (1); i.e a cyclic addition of the two hydrogens either in exact or nearly exact concurrence.