N-substituted benzotriazoles as synthons for 1,3-dipoles

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[7.2.1.0^3,8]dodec-5-ene is also reported. Benzotriazol-1-ylmethylene(benzotriazol-1-ylmethyl)amine does not act as a synthon for the azomethine ylide.