Synthesis and applications of tetrahydro-2-pyridinones via aza-Diels - Alder reactions of thio-substituted 1,3-dienes with arylsulfonyl isocyanates

Article abstract of DOI:10.1055/s-2001-18710

The first aza-Diels - Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of chemo- and regioselectivity. The cyclized products 3a and 5 underwent further reactions with nucleophiles and bases to give useful heterocyclic compounds. The N-tosyl group of the cyclic products could be selectively replaced by hydrogen or another substituent.