Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 14, Issue -, Pages 2799-2804Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.257
Keywords
Baeyer-Mills reaction; bridged azobenzene; diazocine; reductive azo condensation; unsymmetrically functionalized S-diazocines
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Funding
- Deutsche Forschungsgesellschaft (DFG) [Sonderforschungsbereich 677]
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Herein we report a reliable method to synthesize mono-functionalized S-diazocines in reproducible yields via intramolecular Baeyer-Mills reactions. Diazocines exhibit excellent photoswitchable properties. As opposed to azobenzenes they are more stable in their cis configuration. Particularly in photopharmacology mono-functionalized diazocines should be potentially useful and superior to the frequently used azobenzenes because the sterically more demanding cis configuration should be inactive, and the slender trans configuration should fit in a tight binding pocket of a receptor. Hence, it should be possible to administer the stabile inactive compound and switch it on at the site of illness with visible light. To date only a limited number of diazocine derivatives have been published of which most are symmetrically functionalized. Using the Baeyer-Mills reaction for the synthesis of diazocines opens a novel and convenient access to unsymmetrically substituted diazocines.
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