Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

• D. Tyler McQuade^*ab
• Alexander G. O'Brien^a
• Markus Dörr^c
• Rajathees Rajaratnam^c
• Ursula Eisold^d
• Bopanna Monnanda^a
• Tomoya Nobuta^a
• Hans-Gerd Löhmannsröben^d
• Eric Meggers^c
• Peter H. Seebergera^e

• ^a Department for Biomolecular Systems, Max Planck Institute for Colloids and Interfaces
• ^b Department of bChemistry and Biochemistry, Florida State University
• ^c Fachbereich Chemie, Philipps-Universität Marburg
• ^d Potsdam Institut für Chemie
• ^e Freie Universität Berlin

Pyridocarbazoles when ligated to transition metals yield high affinity kinase inhibitors. While batch photocyclizations enable the synthesis of these heterocycles, the non-oxidative Mallory reaction only provides modest yields and difficult to purify mixtures. We demonstrate here that a flow-based Mallory cyclization provides superior results and enables observation of a clear isobestic point. The flow method allowed us to rapidly synthesize ten pyridocarbazoles and for the first time to document their interesting photophysical attributes. Preliminary characterization reveals that these molecules might be a new class of fluorescent bioprobe.

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