Oxidant Mediated Dearomative ipso-Annulation of Bicyclobutanes: Synthesis of spiro-1,4-Cyclohexadienone

Agasti, Souvik (2025) Oxidant Mediated Dearomative ipso-Annulation of Bicyclobutanes: Synthesis of spiro-1,4-Cyclohexadienone. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Souvik Agasti (23MP001)) 23MP001_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (2MB)

Abstract

This study introduces a novel dearomatized aza-spirocycle derived from bicyclobutane carboxamide, showcasing a powerful approach to spirocycle synthesis.1 Using ceric ammonium nitrate as a radical initiator,2 the transformation occurs through oxidative radicalpromoted alkylation and ipso-annulation in a domino process, efficiently constructing two new carbon-carbon bonds. The reaction conditions accommodate diverse radical precursors, such as 1,3-dicarbonyl compounds and sulfinate salts, expanding the method’s versatility. The ability to introduce multiple functionalities in a single step enhances its efficiency for synthesizing complex spirocyclic frameworks. This marks the first application of dearomatized spirocyclization to a bicyclobutane-based molecule,3 unlocking new possibilities for medicinal chemistry and natural product synthesis.4-7 By leveraging strained bicyclobutane systems as precursors, this approach highlights the growing potential of radical-driven strategies in complex molecule construction.

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