Article ; Online: Skeletal Editing of Benzene Motif: Photopromoted Transannulation for Synthesis of DNA-Encoded Seven-Membered Rings.
Organic letters
2024 Volume 26, Issue 11, Page(s) 2212–2217
Abstract: In this report, we present a photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif ... ...
Abstract | In this report, we present a photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif coupled with a Reversible Adsorption to Solid Support (RASS) strategy. A variety of valuable DNA-encoded seven-membered ring compounds, including DNA-encoded 3H-azepines, azepinones, and unnatural amino acids, are now accessible. Crucially, this DNA-compatible protocol can also be applied for the introduction of complex molecules, as exemplified by Lorcaserin and Betahistine. The selective conversion of readily available phenyl rings into high-value seven-membered rings offers a promising avenue for the construction of diversified and drug-like DNA-encoded library. |
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MeSH term(s) | Benzene ; Azides ; Cyclization ; Amines ; DNA |
Chemical Substances | Benzene (J64922108F) ; Azides ; Amines ; DNA (9007-49-2) |
Language | English |
Publishing date | 2024-03-07 |
Publishing country | United States |
Document type | Journal Article |
ISSN | 1523-7052 |
ISSN (online) | 1523-7052 |
DOI | 10.1021/acs.orglett.4c00377 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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