| Autor: |
Pascal Lentes, Jeremy Rudtke, Thomas Griebenow, Rainer Herges |
| Jazyk: |
angličtina |
| Rok vydání: |
2021 |
| Předmět: |
|
| Zdroj: |
Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 1503-1508 (2021) |
| Druh dokumentu: |
article |
| ISSN: |
1860-5397 |
| DOI: |
10.3762/bjoc.17.107 |
| Popis: |
Novel nitrogen-bridged diazocines (triazocines) were synthesized that carry a formyl or an acetyl group at the CH2NR-bridge and bromo- or iodo-substituents at the distant phenyl ring. The photophysical properties were investigated in acetonitrile and water. As compared to previous approaches the yields of the intramolecular azo cyclizations were increased (from ≈40 to 60%) using an oxidative approach starting from the corresponding aniline precursors. The Z→E photoconversion yields in acetonitrile are 80–85% and the thermal half-lives of the metastable E configurations are 31–74 min. Particularly, the high photoconversion yields (≈70%) of the water-soluble diazocines are noteworthy, which makes them promising candidates for applications in photopharmacology. The halogen substituents allow further functionalization via cross-coupling reactions. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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