5310-10-1Relevant articles and documents
Craig et al.
, p. 177,182 (1951)
Contribution of Solvents to Geometrical Preference in the Z/ E Equilibrium of N-Phenylthioacetamide
Song, Shuyi,Hyodo, Tadashi,Ikeda, Hirotaka,Vu, Kim Anh L.,Tang, Yulan,Chan, Erika S.,Otani, Yuko,Inagaki, Satoshi,Yamaguchi, Kentaro,Ohwada, Tomohiko
, p. 1641 - 1660 (2021/06/28)
We studied the Z/E preference of N-phenylthioacetamide (thioacetanilide) derivatives in various solvents by means of 1H NMR spectroscopy, as well as molecular dynamics (MD) and other computational analyses. Our experimental results indicate that the Z/E isomer preference of secondary (NH)thioamides of N-phenylthioacetamides shows substantial solvent dependency, whereas the corresponding amides do not show solvent dependency of the Z/E isomer ratios. Detailed study of the solvent effects based on molecular dynamics simulations revealed that there are two main modes of hydrogen (H)-bond formation between solvent and (NH)thioacetamide, which influence the Z/E isomer preference of (NH)thioamides. DFT calculations of NH-thioamide in the presence of one or two explicit solvent molecules in the continuum solvent model can effectively mimic the solvation by multiple solvent molecules surrounding the thioamide in MD simulations and shed light on the precise nature of the interactions between thioamide and solvent. Orbital interaction analysis showed that, counterintuitively, the Z/E preference of NH-thioacetamides is mainly determined by steric repulsion, while that of sterically congested N-methylthioacetamides is mainly determined by thioamide conjugation.
Facile synthesis of thioamides via P2S5-mediated beckmann rearrangement of oximes
Li, Jiangsheng,Cheng, Chao,Zhang, Xinrui,Li, Zhiwei,Cai, Feifei,Xue, Yuan,Liu, Weidong
, p. 1687 - 1689 (2012/10/29)
A facile and efficient approach to the synthesis of secondary thioamides from ketoximes via Beckmann rearrangement has been established, using phosphorus pentasulfide as a dehydrating and thiating agent. It is also efficient for the preparation of primary thiobenzamide from benzaldoxime. This approach features simple-operation, easy-control and good to excellent yields.
NOVEL PHENYL IMIDAZOLES AND PHENYL TRIAZOLES AS GAMMA-SECRETASE MODULATORS
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Page/Page column 48, (2010/09/18)
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed
