ChemInform Abstract: Synthesis of Azoxyindole Derivatives.

Krichevskii, E. S.; Граник, В. Г.

doi:10.1002/chin.199105201

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“…The oxidation of 8-nitro-g-carbolines (9a, b) by 30% hydrogen peroxide in glacial acetic acid leads to the formation of the corresponding N-oxides 10a, b (Scheme 1) [9].…”

Section: Oxidation and Dehydrationmentioning

confidence: 99%

“…An approach to the functionalization of g-carbolines based on activation of the carbonyl function was described in [9]. Electrophilic attack by phosphorus oxychloride in the presence of triethylamine hydrochloride at the carbonyl group of g-carbolines 49a, b led to the formation of the corresponding chloro derivatives 50a, b, which then reacted with various amines to form amino derivatives 51a-f (Scheme 18).…”

Section: Scheme 16mentioning

confidence: 99%

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Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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Published data on the chemical and biological properties of a-, g-, and d-carbolines are reviewed.Key words: Pyridoindoles (carbolines), chemical and biological properties of carbolines, pK a values of carbolines.Continuing our studies of the properties of carbolines [1], the present study reviews published data on the properties of a-, g-, and d-carbolines. Compounds belonging to different classes of carboline derivatives include many substances with marked biological activity [2, 3].The chemical and physicochemical properties of carbolines have as yet received only fragmentary and insufficient study.The ionization constants of a number of carbolines have been reported [4]. pK a values reflecting the ability of a proton to attach to the pyridine nitrogen atom were obtained, along with constants showing the extent of deprotonation of the indole NH group in carbolines. Table 1 shows that there are significant variations in the ionization constant depending on the structures of the carbolines studied.Information obtained from studies of ionization constants are important for comparing different carbolines. In relation to basicity (protonation of the pyridine nitrogen), it is important to note that the most basic compound in this series is g-carboline. This appears to be due to the greatest level of stabilization of the pyridinium cation due to delocalization of the positive charge by the electron pair of the indole nitrogen:The lowest level of basicity of a-carboline is probably associated with the appearance in the corresponding cation of non-binding interactions between the protons of the pyridinium and indole fragments which destabilize the forming cation.The greatest acidity of g-carboline probably arises by a similar mechanism (increased stabilization of the anion). 389 0091-150X/11/4507-0389

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“…The oxidation of 8-nitro-g-carbolines (9a, b) by 30% hydrogen peroxide in glacial acetic acid leads to the formation of the corresponding N-oxides 10a, b (Scheme 1) [9].…”

Section: Oxidation and Dehydrationmentioning

confidence: 99%

Section: Scheme 16mentioning

confidence: 99%