98215-54-4Relevant academic research and scientific papers
Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation
Perez, Marc,Wu, Zi,Scalone, Michelangelo,Ayad, Tahar,Ratovelomanana-Vidal, Virginie
, p. 6503 - 6514 (2015/10/19)
A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.
Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives
Castro-Castillo, Vicente,Suárez-Rozas, Cristian,Pabón, Adriana,Pérez, Edwin G.,Cassels, Bruce K.,Blair, Silvia
supporting information, p. 327 - 329 (2013/02/23)
Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-re
A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
Kuhakarn, Chutima,Panyachariwat, Nattakan,Ruchirawat, Somsak
, p. 8182 - 8184 (2008/03/14)
A new variation of the Pictet-Spengler reaction for the synthesis of 1-substituted tetrahydroisoquinoline derivatives has been developed. The reaction employs the reduction of N-acylcarbamates by DIBAL-H followed by simultaneous cyclization mediated by BF3·OEt2. The synthetic potential of this method has been illustrated by the synthesis of the tetrahydroisoquinoline alkaloids, (±)-xylopinine, (±)-laudanosine, (±)-8-oxo-O-methylbharatamine, and (±)-isoindoloisoquinolone.
Synthesis and spectral properties of 6,7-dimethoxy-1-[(ortho; and para-R)-phenyl]-3,4-dihydroisoquinoline
Cortes Cortes,Cortes Romero,Gutierrez Ramirez
, p. 1425 - 1427 (2007/10/02)
The preparation of eleven novel 6,7-dimethoxy-1-[(ortho, and para-R)-phenyl]-3,4-dihydroisoquinolines with possible pharmacological activity is described. The structure of all products was corroborated by ir, 1H nmr, 13C-nmr, and ms.
Dehalogenation of 1-Halogenothienyl-di- and -tetra-hydroisoquinolines by Sodium Methoxide in Dimethyl Sulphoxide
Barker, John M.,Huddleston, Patrick R.,Clephane, Janette,Wood, Michael L.,Holmes, David
, p. 275 - 282 (2007/10/02)
On treatment with sodium methoxide-dimethyl sulphoxide (NaOMe-DMSO) 1-(5-halogeno-2-thienyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolines suffer loss of halogen and are converted into the related 1-hydroxytetrahydroisoquinolines.The reaction fails with comparable 1-bromophenyl- and 1-(halogeno-3-thienyl)tetrahydroisoquinolines.A similar transformation takes place with (5-halogeno-2-thienyl)phenylmethoxymethanes, leading to the dimethyl acetal of the 5-dehalogenated-2-thienyl phenyl ketone. α-Halogenated-2 and 3-thienyl-3,4-dihydroisoquinolines undergo dehalogenation-aromatisation with NaOMe-DMSO.Mechanisms for these conversions are proposed.
