Synthesis of Some Halogen‐ and Nitro‐Substituted Nicotinic Acids and Their Fragmentation under Electron Impact.

Dyadyuchenko, L. V.; Стрелков, В. Д.; Mikhailichenko, S. N.; Zaplishny, V. N.

doi:10.1002/chin.200451108

Cited by 2 publications

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“…For the subsequent, deeper stages of fragmentation of compounds 2a-v a distinctive feature is the elimination of a C=O carbonyl fragment by the nicotinoyl cations Φ 1 and Φ 5 , and loss of NO 2 by cations containing it. In further, deeper fragmentation stages elimination of a C≡N group is observed with destruction of the pyridine ring, which is in agreement with already known [4] and established [5] concepts on the fragmentation of pyridine derivatives.…”

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confidence: 90%

Synthesis, Properties, and Special Features of the Fragmentation under Electron Impact of N-Substituted Nicotinoyl Ureas

Dyadyuchenko

Дмитриева

Mikhailichenko

et al. 2005

Chem Heterocycl Compd

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A convenient preparative synthetic route has been developed and N'-substituted nicotinoyl ureas have been obtained for the first time. Possible directions have been studied for their fragmentation under electron impact.Keywords: substituted nicotinoyl isocyanates, N-substituted amines and nicotinoyl ureas, mass spectra.We have synthesized highly reactive nicotinoyl isocyanates from amides of substituted nicotinic acids [1]. In view of the high pesticidal activity of certain substituted ureas [2,3] it seemed expedient to study the possibility of obtaining new substituted ureas from nicotinoyl isocyanates and certain aliphatic and aromatic amines and to investigate their structure and biological activity.Reaction was carried out in absolute benzene with an equimolar ratio of the initial isocyanate and amine according to the following scheme. N Cl R R R O R H R N Cl R R R O NH N R R O N C 1 2 3 4 5 N C C 1 2 3 5 4 1a-v 2a-v = C = O + 1, 2 a-h, o-v R 1 = Me, i-n R 1 = Cl; a-c R 2 = Cl, d-h, m, n, s-v R 2 = NO 2 , i-l, o-r R 2 = H;a-c, s-v R 3 = Me, d-r R 3 = Cl; a-k, m-s, u, v R 4 = H, l R 4 = Et, t R 4 = OMe; a R 5 = i-Pr, b, d, i, m, o R 5 = n-Bu, c, e, j, n R 5 = 4-ClC 6 H 4 , f R 5 = 3,4-Cl 2 C 6 H 3 , g R 5 = 1,2,4-triazol-3-yl, h R 5 = 2-CF 3 C 6 H 4 , k R 5 = 3,4-Cl 2 C 6 H 3 , l R 5 = Et, p R 5 = 4-FC 6 H 4 , q R 5 = 4-ClC 6 H 4 CH 2 , r R 5 = 2,5-Cl 2 C 6 H 3 , s R 5 = Am, t R 5 = Me, u R 5 = 2-ClC 6 H 4 CH 2 , v R 5 = 3-CF 3 C 6 H 4

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confidence: 90%

Synthesis, Properties, and Special Features of the Fragmentation under Electron Impact of N-Substituted Nicotinoyl Ureas

Dyadyuchenko

Дмитриева

Mikhailichenko

et al. 2005

Chem Heterocycl Compd

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“…A solution of 1.4 g (10.6 mmol) of malononitrile dimer 4 and 1.61 g (15.9 mmol) Et3N in 10 mL of acetonitrile was added to a solution of 1.11 g (5.3 mmol) of 4-methyl-2,6-dichloronicotinonitrile 3 [6] in 10 mL of dry acetonitrile. The resulting mixture was boiled for 10.5 h. Then the mixture was evaporated to ~1/2 of the volume and poured into 60 mL of ice water.…”

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confidence: 99%

The reaction of malononitrile dimer with 4-methyl-2,6-dichloronicotinonitrile

Доценко

Muraviev

Dyadyuchenko

et al. 2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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The reaction of 4-methyl-2,6-dichloronicotinonitrile with malononitrile dimer (2-amino-1,1,3-tricyanopropene) in the presence of triethylamine leads to regioselective nucleophilic substitution of the chlorine atom at position 6 and the formation of triethylammonium 2-amino-3-(4-methyl-6-chloro-5-cyanopyridin-2-yl)-1,1,3-tricyanoprop-2-en-1-ide. The structure of the product was confirmed by X-ray studies.

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Synthesis of Some Halogen‐ and Nitro‐Substituted Nicotinic Acids and Their Fragmentation under Electron Impact.

Abstract: With a view to the pharmacologically interesting and pesticidal properties of nicotinic acid derivatives, new polysubstituted analogues, e.g. (III)-(VII), are prepared. -(DYADYUCHENKO, L. V.; STRELKOV, V. D.; MIKHAILICHENKO, S. N.; ZAPLISHNY, V. N.; Chem.

Cited by 2 publications

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Synthesis, Properties, and Special Features of the Fragmentation under Electron Impact of N-Substituted Nicotinoyl Ureas

Synthesis, Properties, and Special Features of the Fragmentation under Electron Impact of N-Substituted Nicotinoyl Ureas

The reaction of malononitrile dimer with 4-methyl-2,6-dichloronicotinonitrile

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