1394823-23-4Relevant articles and documents
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 (2013)
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
Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines
Pilgrim, Ben S.,Gatland, Alice E.,Esteves, Carlos H. A.,McTernan, Charlie T.,Jones, Geraint R.,Tatton, Matthew R.,Procopiou, Panayiotis A.,Donohoe, Timothy J.
, p. 1065 - 1090 (2016/01/15)
The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot isoquinoline synthesis. Alternatively, cyclization of the intermediates with hydroxylamine hydrochloride engenders direct access to isoquinoline N-oxides; and cyclization with methylamine, gives isoquinolinium salts. Significant diversity is available in the substituents at the C4 position in four-component, one-pot couplings, by either trapping the in situ intermediate after α-arylation with carbon or heteroatom-based electrophiles, or by performing an α,α-heterodiarylation to install aryl groups at this position. The α-arylation of nitrile and ester enolates gives access to 3-amino and 3-hydroxyisoquinolines and the α-arylation of tert-butyl cyanoacetate followed by electrophile trapping, decarboxylation and cyclization, C4-functionalized 3-aminoisoquinolines. An oxime directing group can be used to direct a C-H functionalization/bromination, which allows monofunctionalized rather than difunctionalized aryl precursors to be brought through this synthetic route.
An efficient route to polysubstituted tetrahydronaphthols: Silver-catalyzed [4+2] cyclization of 2-alkylbenzaldehydes and alkenes
Zhu, Shifa,Liang, Renxiao,Jiang, Huanfeng,Wu, Wanqing
, p. 10861 - 10865 (2013/01/15)
Silver bullet: A methodology for stereoselective synthesis of polysubstituted tetrahydronaphthols catalyzed by [Ag+]/NPO has been developed. The reactions proceeded through an unprecedented [4+2] cyclization of 2-(2-formylphenyl)ethanone and an alkene, in both inter- and intramolecular fashion. NPO=pyridine N-oxide. Copyright
Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones
Donohoe, Timothy J.,Pilgrim, Ben S.,Jones, Geraint R.,Bassuto, Jose A.
experimental part, p. 11605 - 11608 (2012/09/07)
The utilization of sequential palladium-catalyzed α-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.
