title: C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.
abstract: Cyclic amines such as pyrrolidine and 1,2,3,4-tetrahydroisoquinoline undergo redox-annulations with α,β-unsaturated aldehydes and ketones. Carboxylic acid promoted generation of a conjugated azomethine ylide is followed by 6π-electrocylization, and, in some cases, tautomerization. The resulting ring-fused pyrrolines are readily oxidized to the corresponding pyrroles or reduced to pyrrolidines.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA. seidel@rutchem.rutgers.edu.
authors.forename: YoungKu
authors.initials: Y
authors.lastname: Kang
authors.forename: Matthew T
authors.initials: MT
authors.lastname: Richers
authors.forename: Conrad H
authors.initials: CH
authors.lastname: Sawicki
authors.forename: Daniel
authors.initials: D
authors.lastname: Seidel
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000588:Amines; D001391:Azo Compounds; D002264:Carboxylic Acids; D007546:Isoquinolines; D007659:Ketones; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D002244:Carbon; D006859:Hydrogen; C039109:isoquinoline; C032519:pyrrolidine