320371-79-7Relevant academic research and scientific papers
Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides.
Dai,Larock
, p. 4035 - 4038 (2001)
[reaction: see text] 3,4-Disubstituted isoquinolines have been prepared in good yields by the palladium-catalyzed cross-coupling of N-tert-butyl-o-(1-alkynyl)benzaldimines with aryl, allylic, and alkynyl halides.
Efficient copper(I)-catalyzed, microwave-assisted, one-pot synthesis of 3,4-diaryl isoquinolines
Hu, Zhang,Ou, Li-Li,Li, Si-Dong,Yang, Lei
, p. 3461 - 3469 (2015/06/08)
An efficient copper-catalyzed, microwave-assisted, one-pot reaction has been developed for synthesis of 3,4-diaryl isoquinolines. The reaction was performed in two steps via a CuI/2,2′-biimidazole-catalyzed tandem process from N-tert-butyl-o-iodobenzaldim
Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization
Pilgrim, Ben S.,Gatland, Alice E.,McTernan, Charlie T.,Procopiou, Panayiotis A.,Donohoe, Timothy J.
, p. 6190 - 6193 (2014/01/17)
A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladiu
Application of copper(I) iodide/diorganoyl dichalcogenides to the synthesis of 4-organochalcogen isoquinolines by regioselective C-N and C-chalcogen bond formation
Stein, Andre L.,Bilheri, Filipe N.,Da Rocha, Juliana T.,Zeni, Gilson,Back, Davi F.
, p. 10602 - 10608,7 (2012/12/12)
A copper-catalyzed cyclization of (ortho-alkynyl)benzaldimines with diorganoyl dichalcogenides allowed the synthesis of 4-organochalcogen isoquinolines, whereas the presence of base in the reaction medium inhibited the product formation producing the undesirable isoquinoline without the organochalcogen atom at the 4-position. The cyclization reaction was carried out by using CuI (20 %) as a catalyst with diorganoyl dichalcogenides (1.5 equiv) in the presence of DMF at 100 °C. Furthermore, the reaction did not require an argon atmosphere and was carried out in an open flask. The cyclization reaction tolerated a variety of functional groups both in ortho- alkynylbenzaldimines and diorganoyl dichalcogenides, such as trifluoromethyl, chloro, fluorine, and methoxyl, to give the six-membered heterocyclic ring exclusively through a 6-endo-dig cyclization process. The organochalcogen group present at the 4-position of the isoquinoline ring was further subjected to a selective chalcogen-lithium exchange reaction followed by the addition of aldehydes to afford the desired secondary alcohols in good yields. The obtained isoquinolines also proved to be suitable substrates for the Suzuki and Sonogashira coupling conditions affording the corresponding products through C-C bond formation. Copper-catalyzed cyclization of (ortho-alkynyl)benzaldimines with diorganoyl dichalcogenides enabled the synthesis of 4-organochalcogen isoquinolines (see scheme). The cyclization reaction tolerated a variety of functional groups both in the (ortho-alkynyl)benzaldimines and the diorganoyl dichalcogenides, such as trifluoromethyl, chloro, fluoro and methoxyl, to give the six-membered heterocycle through a 6-endo-dig cyclization process. Copyright
Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-Alkynyl)benzaldimines and organic halides
Dai, Guangxiu,Larock, Richard C.
, p. 920 - 928 (2007/10/03)
The palladium-catalyzed cross-coupling of readily available N-tert-butyl-2-(1-alkynyl)benzaldimines and aryl, allylic, benzylic, alkynyl halides, as well as a vinylic halide, provides a valuable new route to 3,4-disubstituted isoquinolines with aryl, allylic, benzylic, 1-alkynyl, and vinylic substituents, respectively, in the 4-position. The reaction appears to require an aryl group on the end of the acetylene furthest from the imine functionality. The reaction conditions have been optimized, and reasonably good yields have been obtained.
Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines
Dai, Guangxiu,Larock, Richard C.
, p. 7042 - 7047 (2007/10/03)
A number of 3-substituted 4-aroylisoquinolines have been prepared in good yields by treating N-tert-butyl-2-(1-alkynyl)benzaldimines with aryl halides in the presence of CO and a palladium catalyst. Synthetically the methodology provides a simple and convenient route to isoquinolines containing an aryl, alkyl, or vinylic group at C-3 and an aroyl group at C-4 of the isoquinoline ring. The reaction is believed to proceed via cyclization of the alkyne containing a proximate nucleophilic center promoted by an acylpalladium complex.
Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of o-(1-Alkynyl)benzaldimines
Dai, Guangxiu,Larock, Richard C.
, p. 193 - 196 (2007/10/03)
o(1-Alkynyl)benzaldimines react with aryl iodides and 1 atm of CO in the presence of tri-n-butylamine and a Pd(PPh3)4 catalyst to afford good yields of 3-substituted 4-aroylisoquinolines by acylpalladation of the carbon-carbon triple bond and cyclization.
Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation
Croisy-Delcey, Martine,Croisy, Alain,Carrez, Daniele,Huel, Christiane,Chiaroni, Angele,Ducrot, Pierre,Bisagni, Emile,Jin, Lu,Leclercq, Guy
, p. 2629 - 2641 (2007/10/03)
The synthesis of a series of 35 substituted 3,4-diphenyl quinolines and isoquinolines is described. The majority of these molecules differ from all other triphenylethylene based antiestrogens by a different spatial location of the aminoalkyl side chain. T
