28102-51-4Relevant articles and documents
Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes
Buev, Evgeny M.,Stepanov, Maxim A.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
, p. 631 - 635 (2020/01/31)
A methodology for the synthesis of 7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocines from aromatic aldehydes and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine using catalysis by trifluoroacetic and perchloric acids is described. The developed protocol was applied for the synthesis of N-unsubstituted and N-methyl-4-aryltetrahydroisoquinolines.
Medicinally Relevant Modification of the Isoquinoline-1,3-dione Scaffold via Metal-Free Arylation and Fluorination of Diazo Homophthalimides?-in Bronsted Acids
Dar'in, Dmitry,Golushko, Andrei,Guranova, Natalia,Kantin, Grigory,Krasavin, Mikhail,Vasilyev, Aleksander V.
, p. 3815 - 3824 (2019/10/11)
Protonation of 4-diazoisoquinoline-1,3(2 H,4 H)-diones in Bronsted acids gives rise to diazonium cations that can be trapped with arenes to give 4-arylisoquinoline-1,3(2 H,4 H)-diones (homophthalimides). This provides a new, metal-free approach to 4-aryltetrahydroisoquinolines (obtainable from respective homophthalimides by reduction). Similarly, a fluorine atom can be introduced by trapping the diazonium cation with HF. This led to the preparation of the first examples of 4-monofluoro-substituted isoquinoline-1,3-diones (as well as their 4-bromo-4-fluoro and 4-chloro-4-fluoro variants), important carboxylic acid isosteres on their own and precursors of useful 4-fluorotetrahydroisoquinoline building blocks.
Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
Li, Long,Zhou, Bo,Wang, Yong-Heng,Shu, Chao,Pan, Yi-Fei,Lu, Xin,Ye, Long-Wu
supporting information, p. 8245 - 8249 (2015/07/07)
An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.
Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines
Chong, Hyun-Soon,Chen, Yunwei
, p. 5912 - 5915 (2014/01/06)
Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri
Nucleophilic addition of β-amino carbanions to arynes: One-pot synthesis of 4-aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines
Singh, Kamal Nain,Singh, Paramjit,Singh, Pushpinder,Deol, Yadwinder Singh
supporting information; experimental part, p. 2202 - 2205 (2012/06/18)
A novel approach for the direct C-4 arylation of N-methyl-1,2,3,4- tetrahydroisoquinolines by nucleophilic addition of β-aminocarbanions to benzynes is described which provides a one-pot procedure for synthesis of the title compounds.
4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors
Pechulis, Anthony D.,Beck, James P.,Curry, Matt A.,Wolf, Mark A.,Harms, Arthur E.,Xi, Ning,Opalka, Chet,Sweet, Mark P.,Yang, Zhicai,Vellekoop, A. Samuel,Klos, Andrew M.,Crocker, Peter J.,Hassler, Carla,Laws, Mia,Kitchen, Douglas B.,Smith, Mark A.,Olson, Richard E.,Liu, Shuang,Molino, Bruce F.
, p. 7219 - 7222 (2013/01/15)
Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41.
Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
Chernyshov, I. Yu.,Levin,Dilman,Belyakov,Struchkova,Tartakovsky
experimental part, p. 2102 - 2107 (2011/06/26)
A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the
Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates
Crecente-Campo, José,Vázquez-Tato, M. Pilar,Seijas, Julio A.
experimental part, p. 2655 - 2659 (2009/06/20)
An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline and to biologically active 3-benzoazepines as well.
Oxazoline as a useful tool in organic synthesis: Preparation of 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid skeleton
Seijas, Julio A.,Vázquez-Tato, M. Pilar,Martínez, M. Montserrat,Pizzolatti, Moacir G.
, p. 5827 - 5830 (2007/10/03)
New direct strategy for the synthesis of 4-aryl-1,2,3,4- tetrahydroisoquinolines. The key steps are based on oxazoline chemistry: nucleophilic substitution in an ortho-methoxyphenyloxazoline with a Grignard reagent and a 1,6-conjugate addition of a lithiu
Highly stereoselective Friedel-Crafts type cyclization. Facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones
Philippe, Nicolas,Denivet, Fran?ois,Vasse, Jean-Luc,Sopkova-De Olivera Santos, Jana,Levacher, Vincent,Dupas, Georges
, p. 8049 - 8056 (2007/10/03)
The present report describes a stereoselective synthesis of 1,4-dihydro-4-phenyl isoquinolinones 5 based on a stereoselective Friedel-Crafts type cyclization. Cyclization precursors 1 were prepared in two steps, from the readily available (S)-mandelic acid, in 60-80% overall yield. The stereoselective electrophilic cyclization was accomplished in 20-86% yield and with 20-97% ee. In the course of this work, the presence of the amide carbonyl was found to be particularly important to guarantee a stereospecific process during the electrophilic aromatic substitution.
