One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines
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Peer-reviewed
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Abstract
A new, three-step, telescoped reaction sequence for the regioselective conversion of N-tosyl hydrazones and aziridines to 3,6-disubstituted and 3,5,6-trisubstituted 1,2,4-triazines is described. The process involves an efficient nucleophilic ring opening of the aziridine, giving access to a wide range of aminohydrazones, isolated with excellent yields. A “one-pot” procedure, combining the ring opening with a cyclization and an oxidation step, allows the preparation of diversified triazines in good yields.
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0306 Physical Chemistry (incl. Structural)
Journal Title
Organic Letters
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Journal ISSN
1523-7060
1523-7052
1523-7052
Volume Title
19
Publisher
American Chemical Society
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Sponsorship
Engineering and Physical Sciences Research Council (EP/M004120/1)
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K009494/1)
This work was supported by a postdoctoral fellowship from Pfizer (L.C.) and EPSRC Grant Nos. EP/K009494/1 and EP/M004120/1 (S.V.L.). We also thank Dr. Andrew D. Bond for conducting X-ray crystallographic analysis.