137266-01-4Relevant academic research and scientific papers
Halogen-lithium exchange versus deprotonation: synthesis of diboronic acids derived from aryl-benzyl ethers
Kli?, Tomasz,Serwatowski, Janusz
, p. 1169 - 1173 (2007)
Lithiation of a series of aryl benzyl ethers containing halogen substituents (-F, -Br, -I) was investigated. The resultant mono- and diorganolithium intermediates were converted into the corresponding aldehydes or diboronic acids in good yields. The dilit
Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
Dai, Xi-Jie,Engl, Oliver D.,León, Thierry,Buchwald, Stephen L.
supporting information, p. 3407 - 3411 (2019/02/24)
Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki–Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles.
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.
Synthesis and biological evaluation of dibenz[b,f][1,5]oxazocine derivatives for agonist activity at κ-opioid receptor
Mitra, Sudipta,Banerjee, Tuhin Suvro,Hota, Sandip K.,Bhattacharya, Debleena,Das, Sumantra,Chattopadhyay, Partha
scheme or table, p. 1713 - 1720 (2011/05/06)
A short and high yield synthetic route to dibenz[b,f][1,5]oxazocines has been developed using Pd catalyzed intramolecular cycloamination reaction. Receptor binding assay using [125I]-dynorphin demonstrated that one of the derivative, 5b showed
Palladium(0)-catalyzed intramolecular heck reaction: A resourceful route for the synthesis of naphthoxepine naphthoxocine derivatives
Majumdar,Ansary, Inul,Sinha, Biswajit,Chattopadhyay, Buddhadeb
experimental part, p. 3593 - 3602 (2010/03/03)
The synthesis of oxocines and oxepines is difficult. Two efficient protocols have been developed for the construction of naphthoxepine and naphthoxocine derivatives by sequential Wittig olefination and intramolecular Heck reaction. Georg Thieme Verlag Stuttgart.
An efficient synthesis of novel dibenzo-fused nine-membered oxacycles using a sequential Baylis-Hillman reaction and radical cyclization
Majhi, Tirtha Pada,Neogi, Arpita,Ghosh, Soumen,Mukherjee, Alok Kumar,Helliwell, Madeleine,Chattopadhyay, Partha
, p. 94 - 100 (2008/09/20)
A short and high yield synthetic route to novel dibenz[b,g]oxonins, one of which has been characterized by X-ray crystallography, has been developed based on a sequential Baylis-Hillman reaction and radical cyclization. The regioselective radical cyclization followed a 9-endo-trig pathway. Georg Thieme Verlag Stuttgart.
Novel synthesis of oxocine derivatives by Wittig olefination and intramolecular Heck reaction via 8-endo trig cyclization
Majumdar,Chattopadhyay,Sinha
, p. 1319 - 1322 (2008/09/18)
A concise and efficient method for the preparation of oxocine derivatives is described via sequential Wittig and intramolecular Heck reactions. The method is highly regioselective and affords high yields of the products.
Synthesis of heterocycles with MF/Al2O3 base-systems: 2-arylbenzofuranes and 2,3-diarylisoquinolin-1(2H)-ones
Hellwinkel,Goke
, p. 1135 - 1141 (2007/10/02)
2-Benzyloxybenzaldehydes, -acetophenones and -benzophenones substituted in the benzyl part with electron-withdrawing groups, cyclize easily to 2-arylbenzofuranes by using a standardized KF- or CsF-Al2O3 base system. An efficient one-pot synthesis for 2,3-diarylisoquinolin-1(2H)-ones is possible by reacting a variety of arene carbaldehyde anils with phthalides under the same reaction conditions.
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
