1516-73-0Relevant articles and documents
Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides
Gra?l, Simon,Singer, Johannes,Knochel, Paul
, p. 335 - 338 (2019/11/22)
A wide range of alkyl-, aryl- and heteroarylzinc halides were aminated with highly functionalized alkyl, aryl, and heterocyclic azides. The reaction proceeds smoothly at 50 °C within 1 h in the presence of FeCl3 (0.5 equiv) to furnish the corresponding secondary amines in good yields. This method was extended to peptidic azides and provided the arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of pharmaceutical relevance using this iron-mediated electrophilic amination as the key step.
Water compatible photoarylation of amino acids and peptides
Sudakow, Alex,Papke, Uli,Lindel, Thomas
supporting information, p. 10223 - 10226 (2014/08/18)
A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.
Total syntheses of naamine A and naamidine A, marine imidazole alkaloids
Ohta, Shunsaku,Tsuno, Naoki,Nakamura, Seikou,Taguchi, Norio,Yamashita, Masayuki,Kawasaki, Ikuo,Fujieda, Mieko
, p. 1939 - 1955 (2007/10/03)
The first total syntheses of naamine A (4) and naamidine A (5), marine imidazole alkaloids, were achieved through twelve and thirteen steps of reactions, respectively, starting from 1-methyl-2-phenylthio-1H-imidazole (17).
