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Yu, V. К.; Nagimova, A. D.; Пралиев, К. Д.; Shin, S. N.; Kempe, N.

doi:10.1023/a:1021048331427

Cited by 4 publications

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“…Hydrolysis of 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro [4,5]deca-3-ene (4) takes place on refluxing in concentrated hydrochloric acid to yield acid 6 as the only product (47% yield). In the 13 C NMR spectrum of 6, signals due to the double bond (153.3 and 102.1 ppm), the carbons of the piperidine ring (С-5 72.4; С-7 and C-9 49.9; С-6 and C-10 30.3 ppm), the ethoxyethyl substituent (68.0; 65.9; 57.9; 14.3 ppm), and the methyl (10.8 ppm) and methylene of the five-membered ring (72.7 ppm) were present.…”

Section: Scheme 1 Cyanoethylation Followed By Spirocycle Formationmentioning

confidence: 99%

“…Bands typical for a carboxylic group (1716, 1264 and 3098 cm -1 ) were found in the IR spectrum of 6. Thus compound 6 was identified as 3-carboxy-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro [4,5]dec-3-ene.…”

Section: Scheme 1 Cyanoethylation Followed By Spirocycle Formationmentioning

confidence: 99%

“…

Please cite this article as: Yu, V., Praliyev, K., Nagimova, A., Zazybin, A., A simple one-pot synthesis of Nsubstituted 4-methyl-1-oxa-8-azaspiro [4,5]deca-3-en-3-carboxylic acids, Tetrahedron Letters (2015), doi: http:// dx.

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mentioning

confidence: 99%

“…The spirocyclic compounds, 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro [4,5]deca-3-ene and 3-cyano-4-methyl-8-(2-phenylethyl)-1-oxa-8-azaspiro [4.5]dec-3-ene, were unexpectedly obtained from the reaction of 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine and 1-(2-phenylethyl)-4-acetyl-4-hydroxypiperidine with acrylonitrile at room temperature in the presence of an alkali catalyst; further hydrolysis led to the corresponding carboxylic acids. The spirocyclic compounds are thought to form via an aldol condensation which follows cyanoethylation.…”

mentioning

confidence: 99%

“…Besides, Tramadol did not show deep analgesia, while the time of deep analgesia for 1 was 25.0 ± 8.6 minutes. The synthesis of piperidinecarboxylic acid 1 was performed via cyanoethylation of cyclic and heterocyclic compounds, 3,4 followed by hydrolysis of the nitrile group. 5 It was found previously 6 that the introduction of an acetyl group at the C-4 position of a piperidine ring significantly increases the analgesic activity.…”

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confidence: 99%

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A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

Praliyev²,

Nagimova³

et al. 2015

Tetrahedron Letters

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Section: Scheme 1 Cyanoethylation Followed By Spirocycle Formationmentioning

confidence: 99%

Section: Scheme 1 Cyanoethylation Followed By Spirocycle Formationmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

Praliyev²,

Nagimova³

et al. 2015

Tetrahedron Letters

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Synthesis, Antibacterial and Analgesic Activity of 1‐(2‐Ethoxyethyl)‐4‐hydroxy(acyloxy)piperidine‐4‐carboxylic Acids.

Yu¹,

Nagimova²,

Пралиев³

et al. 2002

ChemInform

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Synthesis, Antibacterial and Analgesic Activity of 1-(2-Ethoxyethyl)-4-hydroxy(acyloxy)piperidine-4-carboxylic Acids.-Among the novel compounds prepared, derivatives (III), (VI) and (VIII) possess antibacterial activity, while derivatives (VIII) additionally show an analgesic effect. -(YU, V. K.; NAGIMOVA, A. D.; PRALIEV, K. D.; SHIN, S. N.; DE KIMPE, N.; Khim.-Farm. Zh. 36 (2002) 7, 41-43; Inst. khim. nauk, Minist. nauki Vyssh. Obraz., Almaty, Kazakhstan; RU)

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Thermochemistry of Some Derivatives of 2- and 4-Piperidone

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Cabral

2006

J. Chem. Eng. Data

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Standard (p°) 0.1 MPa) massic energies of combustion for 2-piperidone, 1-methyl-2-piperidone, 1-benzyl-2piperidone, 1-methyl-4-piperidone, 1-ethyl-4-piperidone, and 1-benzyl-4-piperidone were measured at T ) 298.15 K by static bomb calorimetry. The standard molar enthalpies of formation in the condensed phase were derived. The standard molar enthalpies of vaporization at T ) 298.15 K of the piperidone and derivatives studied were determined by high-temperature Calvet microcalorimetry. The respective standard molar enthalpies of formation in the gaseous phase, at T ) 298.15 K, were derived. These results are discussed in terms of molecular structure contributions.

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Cited by 4 publications

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A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

Synthesis, Antibacterial and Analgesic Activity of 1‐(2‐Ethoxyethyl)‐4‐hydroxy(acyloxy)piperidine‐4‐carboxylic Acids.

Thermochemistry of Some Derivatives of 2- and 4-Piperidone

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