3 years ago

Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro-β-carbolines with Aromatic Amines

Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro-β-carbolines with Aromatic Amines
Guolin Wu, Tingting Lv, Haijun Chen, Jinxiang Ye, Yu Gao, Jianlei Wu
The observation of an unexpected oxidative rearrangement coupling reaction led to the development of a novel method for the efficient functionalization of tetrahydro-β-carbolines (THβCs). The treatment of THβCs with photogenerated singlet oxygen (1O2) afforded unstable dioxetanes, which underwent further transformation to form new bonds in the presence of trifluoroacetic acid. This operationally simple protocol exhibits broad functional-group tolerance and is suitable for the late-stage functionalization of complex druglike molecules. All rearrange please: The treatment of tetrahydro-β-carbolines with photogenerated singlet oxygen led to unstable dioxetanes, which underwent ring opening to give synthetic intermediates with a nine-membered ring. These products reacted with amines in the presence of an acid to form a variety of amino-substituted dihydropyrroloquinolines (see scheme). This simple method is suitable for the late-stage functionalization of complex druglike molecules.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708893

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