511244-40-9Relevant academic research and scientific papers
Light-sensitive protecting groups for amines and alcohols: The photosolvolysis of n-substituted 7-nitroindolines
Hassner, Alfred,Yagudayev, Diana,Pradhan, Tarun K.,Nudelman, Abraham,Amit, Boaz
, p. 2405 - 2409 (2007)
Representative examples of primary and secondary amines were protected as urea derivatives 4 of 5-bromo-7-nitroindoline and even more efficiently as ureas 8 derived from 5,7-dinitroindoline, via high-yield reactions with carbamoyl chlorides 3 and 7, respectively. Deprotection of 4 or 8 was achieved in high yields by UV irradiation at room temperature in Pyrex vessels under neutral conditions and exclusion of air. In a similar manner the dinitroindolines serve as protecting groups for alcohols and phenols; the derived carbamates 5 and 9 can likewise be deprotected photochemically in high yields. Georg Thieme Verlag Stuttgart.
Photochemical protection of amines with Cbz and Fmoc groups
Helgen, Celine,Bochet, Christian G.
, p. 2483 - 2486 (2007/10/03)
The photochemical conversion of amines into carbamates was achieved using N-Cbz-, N-Fmoc-, and N-Boc-5,7-dinitroindolines. This reaction allows the protection of amines in neutral medium. Primary and unhindered secondary amines were protected to yield their benzyloxycarbonyl- and 9-fluorenylmethoxycarbonyl derivatives efficiently, whereas bulky amines or anilines gave low yields or no product. On the other hand, the formation of N-Boc compounds, although possible, proceeded only with low yields.
