141438-47-3Relevant academic research and scientific papers
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.
Direct one-pot synthesis of phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction
Young, Ha Kim,Lee, Hyuk,Yeong, Joon Kim,Bum, Tae Kim,Heo, Jung-Nyoung
, p. 495 - 501 (2008/09/17)
(Chemical Equation Presented) We have developed an efficient cascade reaction, a Suzuki-Miyaura coupling followed by an aldol condensation, for the construction of phenanthrene derivatives using microwave irradiation. For example, the reaction of methyl 2-bromophenylacetamide with 2- formylphenylboronic acid in the presence of a palladium catalyst and a base provided a biaryl intermediate, which underwent in situ cyclization to afford the corresponding phenanthrene in high yield.
Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines
Elban, Mark A.,Chapuis, Jean C.,Li, Mei,Hecht, Sidney M.
, p. 6119 - 6125 (2008/03/28)
Described herein is the first total synthesis and structural confirmation of cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluatio
Formamidines in Synthesis. An Efficient One-Pot Synthesis of 7-Substituted Indolines via Intramolecular Cyclization of (2-Phenethyl)formamidines. An Asymmetric Route to Benzopyrrocoline Alkaloids.
Sielecki, Thais M.,Meyers, A. I.
, p. 3673 - 3676 (2007/10/02)
o-Chloro-β-phenethylamines, transformed into the N-tert-butylformamidines, were found to be excellent precursors to indolines following benzyne formation.A series of methoxy-substituted o-chlorophenethylamines containing an N-alkyl or aryl substituent wer
