Synlett 1990; 1990(6): 349-351
DOI: 10.1055/s-1990-21090
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Triazolines XX. Vinyl Azides as Dipolarophiles in 1,3-Dipolar Cycloadditions: Intermolecular Cycloaddition of Hydrazoic Acid and α-Styryl Azide to Give a Tetrazole

Pankaja K. Kadaba*
  • *Medicinal Chemistry and Pharmaceutics College of Pharmacy, A. B. Chandler Medical Center, University of Kentucky, Lexington, Kentucky 40536-0082, USA
Further Information

Publication History

Publication Date:
08 March 2002 (online)

As an example of the use of vinyl azides as dipolarophiles, rather than as 1,3-dipoles, in 1,3-dipolar cycloadditons, the intramolecular cycloaddition of hydrazoic acid to α-styryl azide, leading not to a triazole, as expected, but a tetrazole is reported. The intermediate 5-azidotriazoline undergoes a retro-1,3-cycloaddition with elimination of diazomethane and formation of a highly reactive imidoyl azide which cyclizes to the tetrazole, the driving force being derived from the 5-azido group.

    >