Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (17), p.6685-6690
Main Authors: Andreou, Dimitrios, Essien, Nsikak B, Pubill-Ulldemolins, Cristina, Terzidis, Michael A, Papadopoulos, Athanasios N, Kostakis, George E, Lykakis, Ioannis N
Format: Article
Language:English
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Summary:We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02251