- Preparation of photoactivable amino acid derivatives
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(Chemical Equation Presented) A range of N-protected-R-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-R-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. S
- Debieux, Jean-Luc,Bochet, Christian G.
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supporting information; experimental part
p. 4519 - 4524
(2009/10/17)
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- Light-sensitive protecting groups for amines and alcohols: The photosolvolysis of n-substituted 7-nitroindolines
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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.
- Hassner, Alfred,Yagudayev, Diana,Pradhan, Tarun K.,Nudelman, Abraham,Amit, Boaz
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p. 2405 - 2409
(2008/03/27)
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- The mechanism of photoinduced acylation of amines by N-acyl-5,7- dinitroindoline as determined by time-resolved infrared spectroscopy
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(Chemical Equation Presented) The photochemistry of N-acyl-5,7- dinitroindoline (1) was studied in acetonitrile using nanosecond time-resolved infrared (TRIR) spectroscopy. Upon photolysis, two nearly but not completely overlapping sets of transient IR ba
- Cohen, Andrew D.,Helgen, Celine,Bochet, Christian G.,Toscano, John P.
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p. 2845 - 2848
(2007/10/03)
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- Photochemical protection of amines with Cbz and Fmoc groups
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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.
- Helgen, Celine,Bochet, Christian G.
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p. 2483 - 2486
(2007/10/03)
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