Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia

Article abstract of DOI:10.1055/s-1997-3242

The sequential addition/elimination/cycloammination of 4-pentynones in the presence of benzylamine or ammonia produces 1,2,3,-5-substituted and 2,3,5-substituted pyrroles and fused pyrrole sytems, respectively in good to high yields. The methodology has been extended to the preparation of the 17β-hydroxyandrost-4-ene[3,2-b](1-benzyl-5-methyl)pyrrole.