Diastereoselective reductive amination of pyrazolidinyl alkyl ketones

Свиридова, Л. А.; Golubeva, G. A.; Tavtorkin, Alexander N.; Nelyubina, Yulia V.; Кочетков, К. А.

doi:10.1007/s10593-008-0073-x

Cited by 5 publications

(4 citation statements)

References 13 publications

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“…The TLC on Silufol UV-254 was used to follow the course of reactions. Compound purification was performed using short dry column or flash-chromatography on silica gel (60, Fluka, Honeywell Research Chemicals, Morris Plains, NJ, USA) [ 81 ]. Started indole derivatives were used as purchased from Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

2023

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Indoles and hydantoins are important heterocycles scaffolds which present in numerous bioactive compounds which possess various biological activities. Moreover, they are essential building blocks in organic synthesis, particularly for the preparation of important hybrid molecules. The series of hybrid compounds containing indoles and imidazolidin-2-one moiety with direct С─С bond were synthesized using an amidoalkylation one-pot reaction. All compounds were investigated as a growth regulator for germination, growth and development of wheat seeds (Triticum aestivum L). Their effect on drought resistance at very low concentrations (4 × 10−5 М) was evaluated. The study highlighted identified the leading compounds, 3a and 3e, with higher growth-regulating activity than the indole-auxin analogues.

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Section: Methodsmentioning

confidence: 99%

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

2023

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“…The convenient way of synthesis of the starting compounds in diasteriomerically pure forms had been developed by us earlier (Sviridova et al 2008;Tavtorkin et al 2009). All aforementioned reductive methods were tested for the preparation of polyamines; however, the satisfactory results were obtained only for the borane-tetrahydrofuran complex (Feuer and Brown 1970;Enders et al 1998Enders et al , 1999.…”

Section: Resultsmentioning

confidence: 99%

“…N-N Bond breaking in pure diastereomers of c-hydroxypyrazolidine derivatives 1a, 1b, 2 (produced using the previously described procedure (Sviridova et al 2008) allowed to obtain diastereomerically pure 1,3,5-hydroxydiamines 3a, 3b and 4 ( Fig. 3).…”

Section: Resultsmentioning

confidence: 99%

“…It should be mentioned that in all cases phenyl isothiocyanate interacts with the aliphatic amino group only, thus opening the possibility for regioselective synthesis of polyamine derivatives. To confirm the fact that the reductive cleavage occurred without affecting the stereocenters, we introduced enantiomerically pure (1 0 S, 2 0 S, 3S, 5S)-1-acetyl-5-methyl-2-phenyl-3-[2-(1 0 -phenylethylamine)propyl]pyrazolidine 12 ([a] D = ?23.8 (c = 0.39, CHCl 3 ) obtained as described in (Sviridova et al 2008) into the reaction. As a result, the enantiomerically pure (1 0 S, 2S, 4R, 6S)-4-aniline-6-ethylamino-2-(1-phenylethylamino)heptane 13 was isolated (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines

et al. 2012

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Aliphatic polyamines, being a versatile class of organic compounds, are widely used in many fields of medicine and organic chemistry. However, the general approach to the synthesis of chiral aliphatic polyamines has been still undeveloped. Here, we describe a new method for the synthesis of chiral trifunctional amino compounds, namely hydroxydiamines and triamines. The initial compounds, namely substituted hydroxy- or aminopyrazolidines and pyrazolines, are readily available using convenient stereoselective methods developed earlier by us. The proposed method allows synthesizing of chiral diaminoalcohols and triamines, which are the analogs of a well-known anti-TB drug, namely ethambutol, and cannot be obtained alternatively. The key step of the synthesis is N-N bond cleavage in substituted hydroxy- or aminopyrazolidines and pyrazolines with borane-tetrahydrofuran complex; other known methods for N-N bond cleavage turned out to be ineffective. The main advantage of the proposed method is the retention of a certain configuration of stereocenters in the course of the reaction. Six new chiral diasteomerically pure substituted hydroxydiamines and triamines and the enantiomerically pure triamine with four chiral centers were synthesized and characterized using NMR, IR and mass spectroscopy, as well as elemental analysis.

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