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An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles
1Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, BCC-315 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Organic Letters
|December 12, 2001
Abstract:
[reaction: see text] Fused 5-heterotetrazole ring systems are synthesized in high yield via intramolecular [2 + 3] cycloadditions of organic azides and heteroatom-substituted nitriles. Cyanates, thiocyanates, and cyanamides are all competent dipolarophiles for this reaction. A variety of scaffolds are tolerated when the new enclosed ring is five- or six-membered.