Aza-Diels–Alder Reactions with Lanthanide Triflates: Syntheses of Quinoline and Phenanthridine Derivatives

Abstract

Abstract The aza-Diels–Alder reactions of cyclopentadiene and cyclo-1,3-hexadiene with various substituted N-arylimines in the presence of Yb/Sc triflates as catalyst in MeCN at room temperature gave quinoline and phenanthridine derivatives in moderate to high yields. Some of the cycloaddition reactions were carried out in ionic liquid. Keywords: Aza-Diels–Alderheterocyclic compoundsphenanthridinequinolinetriflates ACKNOWLEDGMENTS We gratefully acknowledge financial support of this research by the Scientific and Technical Research Council of Turkey (TUBITAK) (Project Number 105T421). Notes a Yields of pure isolated products, characterized by FTIR, GC-EIMS, 1H NMR, 13C NMR, and elemental analysis. b With ionic liquid and Sc(OTf)3. c With acetonitrile and Sc(OTf)3. a Yields of pure isolated products, characterized by FTIR, GC-EIMS, 1H NMR, 13C NMR, and elemental analysis. b With acetonitrile and Yb(OTf)3. c With acetonitrile and Sc(OTf)3. d With ionic liquid and Sc(OTf)3.