b-Carboline Alkaloids

Stuart, K. L.; Woo-Ming, Rex B.

doi:10.3987/r-1975-03-0223

Cited by 34 publications

(8 citation statements)

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“…Plots of log 1 against Hgave straight lines whose slopes and correlation coefficients are reported in the Table . It can be noted that the values of these slopes were sufficiently close to unity to permit the conclusion that the ionization of these compounds follows the Hacidity function. Hence, the pK, values were calculated using equation (2) and the data are reported in the Table . As can be seen, the pK, value of harman is fairly independent of the wavelength used for the ionization ratio determination. On the other hand, it is in very good agreement with the value of 14.6 previously reporkd.…”

Section: Scheme Ionization Equilibria Of P-carbolinementioning

confidence: 99%

Ionization of β-carbolines in concentrated hydroxide solutions

Pérez¹,

Guzman²,

Toledo³

et al. 1986

J. Chem. Soc., Perkin Trans. 2

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Section: Scheme Ionization Equilibria Of P-carbolinementioning

confidence: 99%

Ionization of β-carbolines in concentrated hydroxide solutions

Pérez¹,

Guzman²,

Toledo³

et al. 1986

J. Chem. Soc., Perkin Trans. 2

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“…The Pictet–Spengler reaction is an important class of name reaction employed extensively for the synthesis of tetrahydro-β-carboline [1–9]. Typically, the Pictet–Spengler reaction is a two-step reaction.…”

Section: Introductionmentioning

confidence: 99%

Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction

Sharma

Singh²,

Nand³

et al. 2013

Beilstein J. Org. Chem.

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SummaryA practical, mild and efficient protocol for the Pictet–Spengler reaction catalyzed by cyanuric chloride (trichloro-1,3,5-triazine, TCT) is described. The 6-endo cyclization of tryptophan/tryptamine and modified Pictet–Spengler substrates with both electron-withdrawing and electron-donating aldehydes was carried out by using a catalytic amount of TCT (10 mol %) in DMSO under a nitrogen atmosphere. TCT catalyzed the Pictet–Spengler reaction involving electron-donating aldehydes in excellent yield. Thus, it has a distinct advantage over the existing methodologies where electron-donating aldehydes failed to undergo 6-endo cyclization. Our methodology provided broad substrate scope and diversity. This is indeed the first report of the use of TCT as a catalyst for the Pictet–Spengler reaction.

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“…[5] Although poor stereo-control and racemization [6Ϫ8] were observed with tryptophan methyl ester, Cook's group were able to achieve excellent trans stereocontrol by using N-benzyl derivatives of tryptophan. [9] They used this trans-specific PictetϪSpengler reaction as a route to bridged indole alkaloids such as ajmaline (3) from Nbenzyl tryptophan methyl ester [10] by using an epimerization pathway that traps out the desired cis-stereoisomer;…”

Section: Introductionmentioning

confidence: 99%