Syntheses in the isoquinoline series. Synthesis and chemical transformation of 2,3-dihydro-4(1H)-isoquinolones

Grethe, Guenter; Lee, Hsi Lin; Uskoković, Milan R.; Brossi, Arnold

doi:10.1021/jo01266a004

Cited by 32 publications

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“…C'est ainsi qu'ont 6th trouvks plusieurs nouveaux produits qui font maintenant partie de l'arsenal thkrapeutique [4]. Cependant les possibilitCs damCliorer ce que l'on a appelk les (( antidkpresseurs tricycliques )) ne sont nullement CpuisCes.…”

Section: Sunclassified

“…Aus der nachfolgenden Zone wurden 3,82 g (40%) oliges 8-Hydroxy-7-methoxy-7-(4-methoxy-benzyZ)-Z-methyZ-l, 2,3,4- -(4-Hydroxybenzyl)-7,8-dimethoxy-2-rnethyl- II 2,3, vom Smp. [165][166][167][168]) C,,H,,NO,(313,4) Ber. C 72,83 H 7,40 N 4,47y0 Gef.…”

Section: Sunclassified

“…Im Schema 1 sind die Ergebnisse der saurekatalysierten Demethylierung des sekundaren Amins la [4] [5] C,H,,NO,,HCl (201, 7) Ber. C 53,61 H 6,OO N 6,95% Gef.…”

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Eine neue Synthese von Petalin

Grethe

Lee

Uskoković

et al. 1970

Helvetica Chimica Acta

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The structures of the by-products in thc demethylation were determined by the use of nmr. ment (5 -+ 6 ) and the preferential 0-demethylation of 6, is described. and mass spectroscopy.Vor kurzem [2] berichteten wir uber eine einfache Darstellung von l-Benzyl-2-methy1-lI2,3,4-tetrahydro-isochinolinen durch Stevens-Umlagerung der entsprechenden 2-Benzyl-2-methyl-1, 2, 3,4-tetrahydro-isochinolinium-Salze. Gleichzeitig war es uns im Zusammenhang mit Arbeiten uber selektive Atherspaltungen in der Isochinolinreihe gelungen, die 8-Methoxygruppe in 7,8-L)imethoxy-l, 2,3,4-tetrahydro-isochinolinen bevorzugt zu spalten (11. Eine Kombination dieser beiden Befunde fuhrte Schema I

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Section: Sunclassified

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Eine neue Synthese von Petalin

Grethe

Lee

Uskoković

et al. 1970

Helvetica Chimica Acta

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“…The combined organic layers were dried (MgSO 4 ) and concentrated in vacuo.General Procedure 4 (GP 4): The carboxylic acid ester was dissolved in NaOH and stirred for the given time at RT before adjusting the mixture to pH 6 with HCl.1-(4-Methoxy-2-methylphenyl)-1,1-bis(4-methoxyphenyl)methanol (11): According to GP 1: 1-Bromo-4-methoxybenzene (935 mg, 5.00 mmol, 0.63 mL), magnesium (134 mg, 5.50 mmol) in THF (3.8 mL), 4[25] (360 mg, 2.00 mmol) in THF(1 mL), 96 h at RT and flash chromatography (cyclohexane/EtOAc = 9:1). H 2 SO 4 was added, and the resulting mixture was stirred for 5 min at 65 8C.…”

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Development of an (S)‐1‐{2‐[Tris(4‐methoxyphenyl)methoxy]ethyl}piperidine‐3‐carboxylic acid [(S)‐SNAP‐5114] Carba Analogue Inhibitor for Murine γ‐Aminobutyric Acid Transporter Type 4

Pabel

Faust²,

Prehn

et al. 2012

ChemMedChem

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A series of GABA uptake inhibitors related to (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114], the most potent mGAT4 inhibitor known so far, were synthesized and biologically evaluated for their inhibitory potency at the four GABA uptake transporters mGAT1-4 stably expressed in HEK-293 cell lines. New analogues were developed with potencies that are similar to or slightly higher than those of current mGAT4 inhibitors, but with distinctly improved chemical stability. (S)-Nipecotic acid derivatives possessing a 2-[1-(4-methoxy-2-methylphenyl)-1,1-bis(4-methoxyphenyl)methoxy]ethyl (DDPM-859) or a 4,4,4-tris(4-methoxyphenyl)but-2-en-1-yl moiety (DDPM-1457) were found to exhibit pIC(50) values of 5.78 and 5.87, respectively. Thus, as mGAT4 inhibitors, these compounds compare well with (S)-SNAP-5114 (pIC(50) =5.71), but are far more stable than the latter. Moreover, DDPM-859 displays a more favorable subtype selectivity for mGAT4 versus mGAT3 than does (S)-SNAP-5114.

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“…Dagegen waren N-Benzyl-Derivate des 1,2,3,4-Tetrahydroisochinolin-4-ons bereits mit Hg(II)-acetat bei RT zu 4-HydroxyisochinoliniumVerbindungen umgesetzt worden [8]. Dies lässt sich zwanglos aus einer 2,3-Iminium-Zwischenstufe erklä-ren.…”

Section: Ergebnisse Und Diskussionunclassified

Oxidation cyclischer α-Aminoketone / Oxidation of Cyclic α-Aminoketones

Möhrle

Rohn

2007

Zeitschrift Für Naturforschung B

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The 1,2,3,4-tetrahydro-isoquinolin-4-one 4 reacts as an α-amino ketone with periodate to give various products, the major compound being 1-hydroxy-1,2-dihydro-3,4-isoquinolinedione 12. Upon stepwise oxidation with Hg(II)-EDTA the 4-hydroxyisoquinolinium ion 14 is detected as an intermediate and its further oxidation with periodate gives rise to an almost identical product spectrum. Because 12 represents a carbinolamide with an additional 4-carbonyl group, this type was examined first. Acid catalysis was used because the reactive species mostly are iminium ions. With cyclic 1,3-dicarbonyl compounds, 1-substituted derivatives 17a, b are formed. With linear species 1-substitution is also observed, but the tautomeric forms 19a -c are obtained. The stable enones 24a, b result from alkyl ketones by ready autoxidation of the primary products. Base catalysis induces a ring contraction of 12 to the hydroxycarboxylic acid 25. Reaction of 12 with aniline and phenylhydrazine yields the easily oxidizable 1-substitution products 28 and 31.

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Syntheses in the isoquinoline series. Synthesis and chemical transformation of 2,3-dihydro-4(1H)-isoquinolones

Cited by 32 publications

References 0 publications

Eine neue Synthese von Petalin

Eine neue Synthese von Petalin

Development of an (S)‐1‐{2‐[Tris(4‐methoxyphenyl)methoxy]ethyl}piperidine‐3‐carboxylic acid [(S)‐SNAP‐5114] Carba Analogue Inhibitor for Murine γ‐Aminobutyric Acid Transporter Type 4

Oxidation cyclischer α-Aminoketone / Oxidation of Cyclic α-Aminoketones

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