137265-99-7Relevant academic research and scientific papers
A cascade process for the synthesis of: Ortho -formyl allyl aryl ethers and 2 H -chromen-2-ol derivatives from arynes via trapping of o -quinone methide with an activated alkene
Sharma, Abhilash,Gogoi, Pranjal
, p. 333 - 346 (2019/01/10)
A transition-metal free synthetic strategy has been developed for the direct synthesis of ortho-formyl substituted allyl aryl ethers via a cascade three-component coupling of arynes, activated alkene and N,N-dimethylformamide. The reaction proceeds via C-
Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination
Heinz, Christoph,Lutz, J. Patrick,Simmons, Eric M.,Miller, Michael M.,Ewing, William R.,Doyle, Abigail G.
supporting information, p. 2292 - 2300 (2018/02/19)
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.
Intramolecular Addition of Vinyl and Aryl Radicals to Oxime Ethers in the Synthesis of Five-, Six- and Seven-membered Ring Systems
Booth, Susan E.,Jenkins, Paul R.,Swain, Christopher J.,Sweeney, Joseph B.
, p. 3499 - 3508 (2007/10/02)
The oxime ethers 2a-e have been cyclised with Bu3SnH to the alkoxyamino-3-methylidenechromanes 3a-e.Seven-membered ring formation was observed when the oxime ethers 7a, b were converted into the dibenzooxepines 8a, b under similar conditions. 1-Metho
