61341-90-0Relevant academic research and scientific papers
Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines
Jiang, Heng,An, Xiaode,Tong, Kun,Zheng, Tianyi,Zhang, Yan,Yu, Shouyun
supporting information, p. 4055 - 4059 (2015/03/30)
A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.
Phenanthridine synthesis through iron-catalyzed intramolecular N-arylation of O-Acetyl oxime
Deb, Indubhusan,Yoshikai, Naohiko
supporting information, p. 4254 - 4257 (2013/09/12)
O-Acetyl oximes derived from 2′-arylacetophenones undergo N-O bond cleavage/intramolecular N-arylation in the presence of a catalytic amount of iron(III) acetylacetonate in acetic acid. In combination with the conventional cross-coupling or directed C-H arylation, the reaction offers a convenient route to substituted phenanthridines.
Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles
Portela-Cubillo, Fernando,Lymer, James,Scanlan, Eoin M.,Scott, Jackie S.,Walton, John C.
scheme or table, p. 11908 - 11916 (2009/04/06)
Symmetrical and unsymmetrical dioxime oxalates were prepared by treatment of oximes with oxalyl chloride. UV photolysis of these precursors was found to be an atom-efficient way of generating iminyl radicals. The process was most efficient for dioxime oxalates having aryl substituents attached to their C{double bond, long}N bonds. The method was useful for EPR spectroscopic study of iminyl and iminoxyl radicals. Photolyses in toluene solution, of dioxime oxalates containing alkenyl acceptor groups, yielded unsaturated iminyl radicals that ring closed to afford 3,4-dihydro-2H-pyrroles in good yields. Dioxime oxalates with biphenyl substituents also released iminyl radicals that ring closed onto the aromatic acceptor groups and, in acetonitrile solution, this approach provided a useful and atom-efficient method of making substituted phenanthridines.
From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals
Portela-Cubillo, Fernando,Scanlan, Eoin M.,Scott, Jackie S.,Walton, John C.
scheme or table, p. 4189 - 4191 (2009/03/11)
Dioxime oxalates are useful precursors for the clean generation of iminyl radicals by sensitised UV photolysis and can be adapted for serviceable preparations of 3,4-dihydro-2H-pyrroles and phenanthridines. The Royal Society of Chemistry.
