Silver-Catalyzed Cascade Cyclization/1,6-Conjugate Addition of Homopropargyl Sulfonamides to p‑Quinone Methides: An Approach to Diverse 3‑Diarylmethine Substituted Dihydropyrroles

A silver-catalyzed cycloisomerization/1,6-conjugate addition of homopropargyl sulfonamides to p-quinone methides to access diverse diarylmethine substituted dihydropyrroles has been disclosed. The reaction pathway involves an intramolecular cascade cyclization of homopropargyl sulfonamides to genera...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15038-15050
Main Authors: Shirsath, Sachin R, Ghotekar, Ganesh S, Bahadur, Vir, Gonnade, Rajesh G, Muthukrishnan, M
Format: Article
Language:English
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Summary:A silver-catalyzed cycloisomerization/1,6-conjugate addition of homopropargyl sulfonamides to p-quinone methides to access diverse diarylmethine substituted dihydropyrroles has been disclosed. The reaction pathway involves an intramolecular cascade cyclization of homopropargyl sulfonamides to generate a highly reactive dihydropyrrole intermediate in situ followed by conjugate addition with p-quinone methides. This method provides an efficient and scalable route for the synthesis of 3-diarylmethine substituted dihydropyrroles, in one pot.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01922