N-substituted benzotriazoles as synthons for 1,3-dipoles
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2371-2377
- https://doi.org/10.1039/p19900002371
Abstract
N-Bis(benzotriazol-1-ylmethyl)hydroxylamine has been shown to be an effective synthon for the nitrone 1,3-dipole. Regio- and stereo-specific cycloaddition with several dipoiarophiles to furnish substituted 2-(benzotriazol-1-ylmethyl)isoxazolidines is described. Subsequent replacement of the benzotriazole entity is reported, and reaction of the cycloadducts with perchloric acid is shown to yield isoxazolidines without nitrogen substitution. The synthesis of the novel tricyclic ring system 12-oxa-1,3-diazatricyclo[7.2.1.03,8]dodec-5-ene is also reported. Benzotriazol-1-ylmethylene(benzotriazol-1-ylmethyl)amine does not act as a synthon for the azomethine ylide.Keywords
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