18780-56-8Relevant 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.
Identification of tris-(phenylalkyl)amines as new selective h5-HT2B receptor antagonists
Ponnala, Shashikanth,Kapadia, Nirav,Harding, Wayne Wesley
, p. 601 - 605 (2015/04/27)
A series of tris-(phenylalkyl)amines was synthesized and evaluated for affinity to human 5-HT2 receptors. In general, the compounds displayed high affinity (4 of 11 analogs had Ki values 2B receptor vs. other 5-HT2 receptors. Functional assays revealed that the compounds are 5-HT2B antagonists. This journal is
Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method
Zhu, Ruiheng,Xu, Zhangli,Ding, Wei,Liu, Shiling,Shi, Xiaoxin,Lu, Xia
, p. 1039 - 1048 (2016/02/18)
Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.
