Catalyst-free ring opening of azlactones in water microdroplets

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 met...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-11, Vol.6 (9), p.13263-13266
Main Authors: Naveen, Kumar, Rawat, Vishesh Singh, Verma, Rahul, Gnanamani, Elumalai
Format: Article
Language:English
Subjects:
Acetonitrile
Catalysts
Ring opening
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Summary: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. A catalyst-free method was developed for the ring opening of azlactones (also known as oxazolones) in water microdroplets.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc04487h