1620488-58-5Relevant 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
, 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.
Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
Kne?evi?, Anamarija,Vinkovi?, Vladimir,Marakovi?, Nikola,?inko, Goran
, p. 4338 - 4341 (2014/07/22)
In order to synthesize N-(3-azido-1-phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N-substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming a
