1402905-33-2Relevant academic research and scientific papers
Preparation of 6-substituted phenanthridines from o-biaryl ketoximes via the Beckmann rearrangement
Nakamura, Kohei,Kobayashi, Eiji,Moriyama, Katsuhiko,Togo, Hideo
, (2021)
Treatment of anti alkyl o-biaryl ketoximes and anti aryl o-biaryl ketoximes with Tf2O at 120 °C, followed by quenching with Et3N gave 6-alkylphenanthridines and 6-arylphenanthridines in good yields, respectively. These reactions proceeded through the O-triflation of the ketoximes, the Beckmann rearrangement, and the electrophilic cyclization of the formed nitrilium group onto the aromatic ring.
Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
, p. 4941 - 4948 (2019/11/03)
The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
Wu, Yinuo,Wong, Shun Man,Chan, Tek Long,Kwong, Fuk Yee,Mao, Fei
, p. 5306 - 5309,4 (2012/12/12)
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
Wu, Yinuo,Wong, Shun Man,Mao, Fei,Chan, Tek Long,Kwong, Fuk Yee
, p. 5306 - 5309 (2013/01/15)
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
