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Paper | Special issue | Vol 28, No. 2, 1989, pp.1157-1167
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S141
Conversion of Olefins into Five-membered Nitrogen Heterocycles by Radical Cyclization

Derrick L. J. Clive* and Ali Y. Mohammed

*Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada


2-(Phenylseleno)alkyl cyanamides, available in one step from olefins, according to a known procedure, are easily alkylated on nitrogen by allylic and propargylic halides. The products undergo radical cyclization in the presence of a stannane to produce five-membered nitrogen heterocycles by an exo trigonal or exo digonal pathway. The method can be used to make spiro heterocycles and bicyclic compounds with cis ring-fusion geometry.