One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines
American Chemical Society
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Crespin, L., Biancalana, L., Morack, T., Blakemore, D., & Ley, S. (2017). One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines. Organic Letters, 19 (5), 1084-1087. https://doi.org/10.1021/acs.orglett.7b00101
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.
Is supplemented by: https://doi.org/10.17863/CAM.7001
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.
External DOI: https://doi.org/10.1021/acs.orglett.7b00101
This record's URL: https://www.repository.cam.ac.uk/handle/1810/264034
Attribution 4.0 International, Attribution 4.0 International, Attribution 4.0 International, Attribution 4.0 International