88229-12-3Relevant academic research and scientific papers
Diamine Synthesis via the Nitrogen-Directed Azidation of σ- And π-C-C Bonds
Nguyen, Tin V. T.,Wang, Ming-Ming,Waser, Jerome
supporting information, p. 11969 - 11975 (2021/08/24)
Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. We report herein a new strategy giving access to 1,2, 1,3, and 1,4 amido azides as orthogonally protected diamines based on the nitrogen-directed diazidation of alkenes, cyclopropanes, and cyclobutanes. Commercially available copper thiophene-2-carboxylate (CuTc, 2 mol %) as catalyst promoted the diazidation of both πand σ C-C bonds within 10 min in the presence of readily available oxidants and trimethylsilyl azide. Selective substitution of the formed α-amino azide by carbon nucleophiles (electron-rich aromatic, malonate, organosilicon, organoboron, organozinc, and organomagnesium compounds) was then achieved in a one-pot fashion, leading to the formation of 1,2-, 1,3-, and 1,4-diamines with the amino groups protected orthogonally as an amide/carbamate and an azide.
Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis
Wang, Ming-Ming,Waser, Jér?me
supporting information, p. 16420 - 16424 (2020/07/30)
We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the γ or δ position. Both inexpensive benzophenone with UVA light or organic and inorganic dyes with blue light could be used as photoredox catalysts to promote this process. Various fluorinated amines were then obtained by nucleophilic attack on the hemiaminals in one pot, giving access to a broad range of useful building blocks for medicinal chemistry.
Design of novel CSA analogues as potential safeners and fungicides
Zheng, Yang,Liu, Bin,Gou, Zhaopin,Li, Yao,Zhang, Xiao,Wang, Yanqing,Yu, Shujing,Li, Yonghong,Sun, Dequn
supporting information, p. 791 - 794 (2015/02/19)
Study of safeners has been seldom reported in literature. In this work, a series of novel acylsulfamoylbenzamide analogues was designed and synthesized with newly developed safener cyprosulfamide (CSA) as the leading compound. The activity assay against the herbicide thiencarbazone-methyl (TCM) on maize revealed that fifteen compounds showed better protective effect than CSA on the fresh weight of aerial parts, twelve compounds exhibited better activity on the dry weight of aerial parts. Remarkably, two compounds (6Ih, 7II) had protective effect on the four aspects of TCM treated maize. Further antifungal assay showed their excellent activity against Physollospora piricola. The structure-activity relationships of CSA analogues as safeners and fungicides were discussed and it might be valuable for further molecular modification of new CSA analogues.
POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.
Agwada
, p. 231 - 235 (2007/10/02)
The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.
