499109-69-2Relevant academic research and scientific papers
Mild and efficient syntheses of 1-aryl-3,4-dihydroisoquinolines and 1-aryl-3,4-dihydro-β-carbolines via regiospecific β-eliminations of the corresponding N-tosyl-1,2,3,4-tetrahydroisoquinolines and N-tosyl-1,2,3,4-tetrahydro-β-carbolines
Dong, Jing,Shi, Xiao-Xin,Xing, Jing,Yan, Jing-Jing
experimental part, p. 2806 - 2817 (2012/07/16)
(Chemical Equation Presented) Treatment of N-tosyl-1-aryl-1,2,3,4- tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-β-carbolines with a strong base such as NaOH or KOH at 70 °C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-β- carbolines in good yields via mild and regiospecific β-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 °C. Copyright Taylor & Francis Group, LLC.
Efficient and practical one-pot conversions of n- tosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-β- carbolines into β-carbolines through tandem β-elimination and aromatization
Dong, Jing,Shi, Xiao-Xin,Yan, Jing-Jing,Xing, Jing,Zhang, Qiang,Xiao, Sen
body text, p. 6987 - 6992 (2011/02/24)
An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines in good to high yields. Both one-pot conversions occurred through tandem β-elimination and aromatization. An efficient method for conversions ofN-tosyltetrahydroisoquinolines (N-tosyl-THIQs) and N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into isoquinolines and β-carbolines is described. Treatment ofN-tosyl-THIQs or N-tosyl-THBCs with base affords dihydroisoquinolines or dihydro-β- carbolines. These can be oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines. Copyright
A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid
Ivanov, Iliyan,Nikolova, Stoyanka,Statkova-Abeghe, Stela
, p. 2483 - 2492 (2007/10/03)
A number of 1-substituted 3,4-dihydro-9H-β-carboline derivatives (4) with high purity and yields have been synthesized by treating of tryptamine (1) with carboxylic acids (2) in polyphosphoric acid. 3,4-Dihydro-9H-β-carbolines (4) were successfully transformed to 1,2,3,4-tetrahydro-9H-β-carbolines (5) and 9H-β-carbolines (6).{A figure is presented}.
The preparation and evaluation of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives as potential antitumor agents
Shen, Ya-Ching,Chen, Ching-Yeu,Hsieh, Pei-Wen,Duh, Chang-Yih,Lin, Yat-Min,Ko, Chin-Lien
, p. 32 - 36 (2007/10/03)
A series of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β- carboline derivatives have been synthesized and evaluated for antitumor activity against murine P-388 and human tumor cell lines, KB-16, A-549 and HT-29. All of the compounds prepared, excep
1-substituted 1,2,3,4-tetrahydro-beta-carboline and 3,4-dihydro-beta-carboline and analogs as antitumor agents
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, (2008/06/13)
A composition includes a substituted dihydro- or tetrahydro-β-carboline of formula (II) or (III), wherein the aromatic ring of the carboline may include one or more substituents selected from the group consisting of hydroxy, C1-6 alkoxy, benzyloxy, C1-6 acyloxy, amino, C1-6 alkyl, C1-6 dialkylamino, halogen, and carboxy, and the C-1 position of the carboline may include a substitutent selected from the group consisting of a carbocyclic group and a heterocyclic group. The composition may include a salt or a prodrug of the substituted dihydro- or tetrahydro-β-carboline. The composition may further includes a pharmaceutically acceptable carrier, diluent, or excipient.
