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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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
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cited_by cdi_FETCH-LOGICAL-a367t-587938dd2317265ee583288664d4b3ff6c2983f9d8cb0e7fcb071d64e29d95fd3
cites cdi_FETCH-LOGICAL-a367t-587938dd2317265ee583288664d4b3ff6c2983f9d8cb0e7fcb071d64e29d95fd3
container_end_page 6690
container_issue 17
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container_title Organic letters
container_volume 23
creator Andreou, Dimitrios
Essien, Nsikak B
Pubill-Ulldemolins, Cristina
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Lykakis, Ioannis N
description 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.
doi_str_mv 10.1021/acs.orglett.1c02251
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title Skeletally Tunable Seven-Membered-Ring Fused Pyrroles
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