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Updated: Jul 18, 2025

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δ-Acetoxy Allenoate as a 5C-Synthon in Domino-Annulation with Sulfamidate Imines: Ready Access to Coumarins
Sachin Chauhan1, A Sanjeeva Kumar1, K C Kumara Swamy1
1School of Chemistry, University of Hyderabad, Hyderabad 500046, Telangana, India.
Abstract:
A DMAP-catalyzed sequential benzannulation and lactonization strategy in which δ-acetoxy allenoate functions as a 5C-synthon in its reaction with cyclic sulfamidate imines is reported. This platform delivers π-extended coumarin frameworks under metal-free conditions via allylic elimination followed by Mannich coupling, proton shifts, C-N bond cleavage, and lactonization as key steps. The driving force for this domino reaction is the formation of the diene-ammonium intermediate and O-S bond cleavage. ESI-HRMS has been useful in gaining insights into the reaction pathway.
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