An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles.
[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.
Demko
Z P
ZP
Department 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.
Sharpless
K B
KB
D003484:Cyanamide / Q000737:chemistry; D003485:Cyanates / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
D003485:Cyanates; D013777:Tetrazoles; D003484:Cyanamide