Cyclodehydrations leading to indene products having N-heterocyclic substituents.
In this Note, we describe superacid-promoted cyclodehydrations leading to functionalized indenes. The product indenes are synthesized having N-heterocyclic substituents, including pyridyl, imidazolyl, pyrimdyl, and other groups. A mechanism is proposed involving dicationic, superelectrophilic intermediates. The protonated N-heterocyclic rings are shown to dramatically lower the LUMO energy level of the carboxonium electrophile (compared to that of a similar uncharged system).
Department of Chemistry and Biochemistry, Northern Illinois University , DeKalb, Illinois 60115, United States.
Kenneth N
KN
Boblak
Douglas A
DA
Klumpp
D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007192:Indenes; C093581:indene