Synthese von Isochinolin‐Derivaten

Späth, Ernst; Berger, Franz; Kuntara, Wilhelm

doi:10.1002/cber.19300630119

Cited by 36 publications

(15 citation statements)

References 3 publications

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“…40. 1962 The difficulties eilcouiltered in the purification of the bases are in line with experience with analogous compou~lds of the dihydroisoquinoline series (7). A trimer, corresponding in structure to N,N1,N"-tripl~enylethyla~~~inomalonaide (8), a substance obtained as a by-product in the cyclodehydratio~l of N-fori~~ylphenylethylamine, was not detected in the intractable by-products of the present preparations.…”

supporting

confidence: 75%

3,4-Dihydro-Β-Carbolines: II. THE EXHAUSTIVE METHYLATION OF 3,4-Dihydro-Β-Carboline

Gupta¹,

Spenser²

1962

Can. J. Chem.

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The n~ethiodide of 3,4-dihydro-0-carboline yields a dimeric anhydro base which, on heating, disproportionates to a 0-carboline and a tetrahydro-p-carboline derivative, and on nlethylation is co11verted to 3-[3-forrnylindolyl]-~-ethyltrin1ethylan1111oni~n iodide.Although a large number of 1-substituted 3,4-dihydro-@-carbolines have beell synthesized (1, 2), the parent base itself (11, R=H) has not been well characterized. 3,4-Dihydro-P-carboline was first obtained (3) by degradation of evodiainine. I t was isolated a s a tarry mass, which yielded a picrate, and was identified by oxidation to Pcarboline (4). Atteinptecl synthesis by conventioiial Bischler-Napieralslti ring closure of NB-forii~~7ltryptarnine (I, R = H ) gave an uiicharacterized product in 2y0 yield (2). The base was later obtained by this inethod in 36y0 yield as an amorphous powder of indeterminate melting point, yielding a picrate and a perchlorate (5).Crude 3,4-dihydro-p-carboline (11, R = H ) has now been obtained in SOY0 yield froill NB-forniyltryptarnine (I, R = H ) , using polyphosphoric acid as the dehydrating agent. The conipound resisted purification because of its sensitivity towards aqueous acid and its tendency to polymerization. Analysis of the free base was unsatisfactory. The inethiodide, however, showed the expected composition. 9-Methyl-3,4-dihydro-P-carboline (11, R = CHJ, obtained from N8-for~nyl-1-inethyltryptamine (I, R = CH3), behaved similarly. The ultraviolet absorption curves of both compounds (Fig. 1) were similar to those of 1-alkyl-3,4-dihydro-P-carbolines (6), and the infrared spectra were also consistent with the assigned structure.

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supporting

confidence: 75%

3,4-Dihydro-Β-Carbolines: II. THE EXHAUSTIVE METHYLATION OF 3,4-Dihydro-Β-Carboline

Gupta¹,

Spenser²

1962

Can. J. Chem.

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“…Several recrystns from petr ether raised the mp to 76-77°. The 4methyl-l-acetoxymethylisoquinoline (11) was possibly contaminated with the 4-acetoxymethyl isomer and was purified after acid hydrolysis.…”

Section: Methodsmentioning

confidence: 99%

“…Treatment of 1,4-dimethylisoquinoline Moxide (8) with Ac20 (Scheme II) produced mainly 4-methyl-1 -acetoxymethylisoquinoline (11). Aminov isomer, possibly 1-methyl-4-acetoxymethylisoquinoline, was present as a contaminant.…”

mentioning

confidence: 99%

Potential antitumor agents. 5. Methylated .alpha.-(N)-heterocyclic carboxaldehyde thiosemicarbazones

Kc¹,

Rj²,

Lipsky³

et al. 1972

J. Med. Chem.

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Several monomethylated derivatives of a-(N)-heterocyclic carboxaldehyde thiosemicarbazones were prepared to define the molecular dimensions compatible with antineoplastic activity. These were the thiosemicarbazones of 3-, 4-, and 5-methylisoquinoline-l-carboxaldehyde and of 3-, 4-, 5-, and 6-methylpyridine-2-carboxaldehyde. Tests for tumor-inhibitory potency indicate that in general the pyridine derivatives were better inhibitors of the growth of the LI210 lymphoma than were the isoquinolines. Introduction of a 6-Me group in the pyridine ring and of an analogous 3-Me substituent in the isoquinoline structure resulted in compounds with no antineoplastic activity indicating an apparent intolerance to substitution at the a position to the heterocyclic N atom for inhibitory action. Me substituents at the other positions of these ring systems did not significantly increase the carcinostatic potency of the parent compounds.

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“…Cizloro-l-zsoPitzno2Bznes La mCthyl-5-isoquinolCine a CtC obtenuc i partir de 1'0-xylhne [29] (6 dtapcs -…”

mentioning

confidence: 99%

Synthèse d'isocarbostyriles et de chloro‐1‐isoquinoléines

Eloy

Deryckere

1969

Helvetica Chimica Acta

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Synthese von Isochinolin‐Derivaten

Cited by 36 publications

References 3 publications

3,4-Dihydro-Β-Carbolines: II. THE EXHAUSTIVE METHYLATION OF 3,4-Dihydro-Β-Carboline

3,4-Dihydro-Β-Carbolines: II. THE EXHAUSTIVE METHYLATION OF 3,4-Dihydro-Β-Carboline

Potential antitumor agents. 5. Methylated .alpha.-(N)-heterocyclic carboxaldehyde thiosemicarbazones

Synthèse d'isocarbostyriles et de chloro‐1‐isoquinoléines

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