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One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines

Published version
Peer-reviewed

Type

Article

Change log

Authors

Biancalana, L 
Morack, T 
Blakemore, DC 
Ley, SV 

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.

Description

Keywords

0306 Physical Chemistry (incl. Structural)

Journal Title

Organic Letters

Conference Name

Journal ISSN

1523-7060
1523-7052

Volume Title

19

Publisher

American Chemical Society
Sponsorship
Engineering and Physical Sciences Research Council (EP/M004120/1)
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.
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