A thermal dehydrogenative Diels-Alder reaction of styrenes for the concise synthesis of functionalized naphthalenes.
Functionalized naphthalenes are valuable building blocks in many important areas. A microwave-assisted, intramolecular dehydrogenative Diels-Alder reaction of styrenyl derivatives to provide cyclopenta[b]naphthalene substructures not previously accessible using existing synthetic methods is described. The synthetic utility of these uniquely functionalized naphthalenes was demonstrated by a single-step conversion of one of these cycloadducts to a fluorophore bearing a structural resemblance to Prodan.
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Laura S
LS
Kocsis
Erica
E
Benedetti
Kay M
KM
Brummond
D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013343:Styrenes / Q000737:chemistry*
D005456:Fluorescent Dyes; D009281:Naphthalenes; D013343:Styrenes