48218-32-2Relevant academic research and scientific papers
A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination
Guo, Sheng,Yang, Jeffrey C.,Buchwald, Stephen L.
supporting information, p. 15976 - 15984 (2018/11/23)
A mild and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1,2-benzisoxazole as a practical electrophilic primary amine source. Using this heterocycle as a new amino group delivery agent, a mild and general protocol for the copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines was developed. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines, as demonstrated by the efficient synthesis of the antiretroviral drug maraviroc and the formal synthesis of several other pharmaceutical agents.
Mitsunobu Reaction Using Basic Amines as Pronucleophiles
Huang, Hai,Kang, Jun Yong
, p. 6604 - 6614 (2017/07/15)
A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.
A highly predictive 3D-QSAR model for binding to the voltage-gated sodium channel: Design of potent new ligands
Zha, Congxiang,Brown, George B.,Brouillette, Wayne J.
, p. 95 - 104 (2014/01/17)
A comprehensive comparative molecular field analysis (CoMFA) model for the binding of ligands to the neuronal voltage-gated sodium channel was generated based on 67 diverse compounds. Earlier published CoMFA models for this target provided μM ligands, but the improved model described here provided structurally novel compounds with low nM IC50. For example, new compounds 94 and 95 had IC50 values of 129 and 119 nM, respectively.
