13372-62-8Relevant articles and documents
Reductive lithiation of a trimethyl benzo-1,3-thiazoline: Generation of an α-amino tertiary carbanion and reactions with electrophiles
Florio,Florio, Saverlo,Capriati,Capriati, Vito,Gallo,Gallo, Antonio,Cohen,Cohen, Theodore
, p. 4463 - 4466 (1995)
Trimethylbenzothiazoline 1 has been reductively lithiated by lithium 4,4'-di-t-butylbiphenylide (LDBB) leading to dianion 3, that has been trapped with electrophiles to give aminodisulfides 4, aminosulfide 8 and aminoalcohols 9.
Iodine-promoted ring-opening methylation of benzothiazoles with dimethyl sulfite
Guo, Ying-Qiong,Chen, Fan,Deng, Chen-Liang,Zhang, Xing-Guo
, p. 1923 - 1926 (2021/03/02)
A halogen-bond promoted ring-opening methylation of benzothiazoles has been developed using dimethyl sulphite as a methylating reagent in the presence of a base. This approach represents a simple and efficient synthesis ofN-methyl-N-(o-methylthio)phenyl amides, and features direct construction of both N-Me and S-Me bonds in a one-pot reaction through the decomposition of easily prepared benzothiazoles.
N -Methylation of ortho -substituted aromatic amines with methanol catalyzed by 2-arylbenzo [d] oxazole NHC-Ir(iii) complexes
Huang, Shuang,Hong, Xi,Cui, He-Zhen,Zhou, Quan,Lin, Yue-Jian,Hou, Xiu-Feng
, p. 5072 - 5082 (2019/04/17)
Seven new chelated cyclometalated Ir complexes of ABON,P, ABON,O, and ABON,C(carbene) based on a rigid and tunable 2-arylbenzo[d]oxazole backbone have been prepared for the N-methylation of amines. Among these three coordinated modes, ABON,C(carbene)-chelated iridium-based catalysts exhibited good performance in the monomethylation of aromatic amines with methanol (MeOH) as the green methylation reagent. The steric-modified synthesis of ABON,C(carbene) complexes was described. The most active ABON,C(carbene) complex with marginal steric hindrance as a catalyst was obtained from the benzoxazole ring without a substituent and methyl group of the benzimidazole ring on the N-heterocyclic carbene (NHC) ligand. A variety of amines including para- and meta-substituted aromatic amines, as well as heterocyclic amines, were formulated as suitable substrates. Importantly, this catalyst considerably promoted the yield of the N-methylation of ortho-substituted aromatic amines. Controlled kinetic experiments and deuterium-labeling reactions of these ortho-substituted amines were conducted under optimized conditions. On the basis of the experimental results, a plausible mechanism was proposed.
