Alkylation of methylene-active compounds with halo acetals and hydrolysis of the alkylation products

Ismailov, V. M.; Yusubov, N. N.; Sadykhova, N. D.; Gasymov, R. A.; Ibragimova, G. G.; Мамедов, И. Г.

doi:10.1134/s1070428016100031

Cited by 5 publications

(2 citation statements)

References 2 publications

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“…A distinctive feature of this reaction from the previous study [7] is that the active methylene group of one molecule joins two nitrile fragments of the second and third molecules of ethyl cyanoacetate, forming diiminoderivative 2 according to the trend as follows:…”

Section: Resultsmentioning

confidence: 93%

Synthesis Based on Ethyl Cyanoacetate

Ismailov,

Yusubov,

Sadykhova

et al. 2023

Chemical Problems

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It has been shown that self-condensation ethyl cyanoacetate under conditions of excess potash in DMSO undergoes an intermolecular Claisen-type condensation involving three substrate molecules to form ethyl 2,4-dicyano-2-[2-cyanoacetyl-3-oxo]-butanoate. Self-condensation ethyl cyanoacetate takes place in the presence of triethyl phosphite and zinc acetate with the participation of three reagent molecules resulting in triethyl 3-cyano-2,4-diiminopentane-1,3,5-tricarboxylate. Alkylation ethyl cyanoacetate with 1,2- dichloroethane, cycloalkylation products were obtained: cyclopropane and cyclohexane derivatives, as well as a polymer product. The reaction of ethyl cyanoacetate with 1,2,3-trichloropropane occurs in a 2:3 ratio giving ethyl 7-chloro-2-(2-chloroallyl)-2,5-dicyano-3-methylenoate-7-enoate and 2,5-bis(2-chloroallyl)-3- methylenehexanedinitrile.

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Section: Resultsmentioning

confidence: 93%

Synthesis Based on Ethyl Cyanoacetate

Ismailov,

Yusubov,

Sadykhova

et al. 2023

Chemical Problems

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“…Ethyl 2‐methylfuran‐3‐carboxylate (9 a) : yellow oil; 1 H (400 Hz, DMSO‐ d 6 , 25 °C): δ =1.28 (t, J =7.2 Hz, 3H), 2.54 (s, 3H), 4.22 (q, J =7.2 Hz, 2H), 6.66 (d, J =2.0 Hz, 1H), 7.59 ppm (d, J =2.0 Hz, 1H); 13 C NMR (100 Hz, DMSO‐ d 6 , 25 °C): δ =13.8, 14.6, 60.2, 110.8, 113.5, 141.9, 159.0, 163.6 ppm.…”

Section: Methodsmentioning

confidence: 99%

Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α‐Bromoacetaldehyde Acetals

Huang

Yiliqi

et al. 2018

Adv Synth Catal

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Benzo[a]carbazoles were synthesized from 2-phenylindoles and a-bromoacetaldehyde using bismuth trichloride as a catalyst. The reaction was triggered by a bismuth trichloride-catalyzed Friedel-Crafts alkylation of these two precursors, which provided a tryptaldehyde intermediate that underwent intramolecular olefination to form the final product. Interestingly, the HBr byproduct generated in the upstream step of the reaction catalyzed the following downstream reaction steps, thus creating a byproduct-participated relay catalytic process. Motivated by this mechanism, we developed a three-component reaction of indole, abromoacetaldehyde acetal, and 1,3-dicarbonyl compounds. This study offers a straightforward method for synthesizing substituted carbazoles.

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Fluorescent 2-carbonyl carbazole ketones: Photophysical properties, molecular structure and selective detection of Fe3+ ion

Du,

Gao,

et al. 2024

Journal of Molecular Structure

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Alkylation of methylene-active compounds with halo acetals and hydrolysis of the alkylation products

Cited by 5 publications

References 2 publications

Synthesis Based on Ethyl Cyanoacetate

Synthesis Based on Ethyl Cyanoacetate

Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α‐Bromoacetaldehyde Acetals

Fluorescent 2-carbonyl carbazole ketones: Photophysical properties, molecular structure and selective detection of Fe3+ ion

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