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Updated: Jun 9, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Catalyst-free ring opening of azlactones in water microdroplets
Kumar Naveen1, Vishesh Singh Rawat1, Rahul Verma1
1Asymmetric Synthesis and Catalysis Laboratory, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttarakhand, India. gnanam@cy.iitr.ac.in.
Abstract:
A catalyst-free method was developed for the ring opening of azlactones (also known as oxazolones) in water microdroplets. Azlactone was dissolved in a water : acetonitrile (1 : 1) mixture, and the solution is sprayed by using nitrogen gas at a pressure of 120 psi to generate microdroplets. This method promoted selective cleavage of the lactone bond to afford the corresponding N-benzoyl derivatives in up to 94% isolated yield with no epimerization. Our method produces the ring-opening products in milliseconds (up to 94 μmol for 33.3 minutes), and may have utility for high-throughput synthesis applications.
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