Cyclocondensation of 2-Aminobenzimidazole with Dimedone and Its Arylidene Derivatives

Липсон, В. В.; Десенко, С. М.; Shishkina, S. V.; Широбокова, М. Г.; Шишкин, Олег В.; Orlov, V. D.

doi:10.1023/b:cohc.0000003522.71893.77

Cited by 41 publications

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“…1 H NMR spectrum, δ, ppm (J, Hz): 4.16 (2Н, q, 3 J = 6.8, СН 2 О); 4.1 (2Н, q, 3 J = 6.8, СН 2 О); 2.57 (1Н, dd, 3 J = 7.4, 3 J = 7.4, СН); 2.21 (3Н, s, СН 3 ); 1.78 and 1.65 (each 1H, m, CH 2 in ring); 1.22 (3Н, t, 3 J = 6.8, СН 3 ); 1.18 (3Н, t, 3 J = 6.8, СН 3 ). 13 1,1-Diacetyl-2-ethoxycarbonylcyclopropane (8). This compound was obtained from a mixture of acetylacetone (5 g, 0.05 mol), ethyl 2,3-dibromopropionate (13 g, 0.05 mol), and K 2 CO 3 (22 g, 0.16 mol) with a yield of 4.5 g (45.5%); bp 120-121°C (1 mm Hg), n D 20 1.4635.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectrum, δ, ppm (J, Hz): 4.05 (2Н, q, 3 J = 6.8, СН 2 О); 2.61 (1Н, m, СН); 2.17 (3Н, s, СН 3 ); 2.15 (3Н, s, СН 3 ); 1.82 and 1.73 (each 1H, m, CH 2 in ring); 1.2 (3Н, t, 3 J = 6.8, СН 3 ). 13 …”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectrum, δ, ppm (J, Hz): 5.82 (1Н, m, СН=); 5.20 and 5.08 (2Н, dd, 3 J cis = 10.2, 3 J trans = 16.9; СН 2 =); 4.30 (1Н, s, ОН); 4.14 (1Н, q, 3 J = 7.8, ОСН); 2.48 (2Н, d, 3 J = 9.5, СН 2 ); 2.33 and 2.15 (each 3Н, s, СН 3 ). 13 4-(2-Acetoxybut-3-enyl)-3,5-dimethylisoxazole (12). To a solution of compound 11 (2 g, 0.012 mol) in CCl 4 (10 ml) we added acetyl chloride (1 g, 0.0127 mol).…”

Section: -(2-hydroxybut-3-enyl)-35-dimethylisoxazole (11)mentioning

confidence: 99%

“…However, only 4-acetyl-5-methyl-2-vinyl-2,3-dihydrofuran (10) is formed in the reaction of dimedone with dibromobutene 2. Derivatives of isoxazole are widely used in the synthesis of medicinal products (oxacillin, cloxacillin, cycloserine) [11] and also natural compounds [12,13].…”

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confidence: 99%

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Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

Maharramov

Sadikhova

Mammadov

et al. 2009

Chem Heterocycl Comp

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The alkylation of some representatives of β-dicarbonyl compounds by 1,4-dibromo-2-butene and ethyl 2,3-dibromopropionate was investigated.Furans represent one of the important classes of heteroaromatic compounds. Substituted furans are usually synthesized by the regioselective insertion of carbon substituents into furan or its acyclic precursors [1]. Universal and convenient synthons for the "construction" of furans and related heterocycles containing an acyl group at position 3 of the heterocycle are β-dicarbonyl compounds. In recent years [2-4] a series of reviews have been published on numerous methods for the synthesis of furans from 1,3-diketones, which are valuable intermediates in the synthesis of liquid crystals, various heterocycles, and physiologically active substances and particularly pheromones and prostaglandins [5][6][7][8].We investigated the alkylation of some representatives of β-dicarbonyl compounds by various dihalides in order to obtain functionally substituted dihydrofurans.While continuing study of the reactivity of β-dicarbonyl compounds [9, 10] we realized the reactions of dimedone, allyl acetoacetate, acetylacetone, and acetoacetic ester with ethyl 2,3-dibromopropionate (1) and 1,4-dibromo-2-butene (2) in the K 2 CO 3 -DMSO system. It was established that the alkylation of dimedone with compounds 1 (Scheme 1) and 2 (Scheme 2) takes place exclusively in the direction of C,O-cycloalkylation with the formation of 2-ethoxycarbonyl-6,6-dimethyl-2,3,4,5,6,7-hexahydrobenzo[b]furan-4-one (3) and 6,6-dimethyl-2-vinyl-2,3,4,5,6,7-hexahydrobenzo[b]furan-4-one (9) respectively.In the reaction of allyl acetoacetate with the ester 1 we obtained 4-allyloxycarbonyl-2-ethoxycarbonyl-5-methyl-2,3-dihydrofuran (4).

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: -(2-hydroxybut-3-enyl)-35-dimethylisoxazole (11)mentioning

confidence: 99%

mentioning

confidence: 99%

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Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

Maharramov

Sadikhova

Mammadov

et al. 2009

Chem Heterocycl Comp

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“…In view of the importance of these polyheterocyclic compounds, several methods have been quoted in the literature [8][9][10][11][12]. However, these methods suffer from drawbacks such as prolonged reaction time, use of volatile organicsolvents, harmful catalysts, low yields and harsh reactionconditions.…”

Section: Introductionmentioning

confidence: 99%

A three-component one-pot procedure for the synthesis benzimidazolo-quinazolinone derivatives in the presence of chitosan-supported metal nanocomposite as a green and reusable catalyst

Maleki

Ghamari

2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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A simple and convenient approach for the synthesis of tetraheterocyclic benzimidazolo [2,3-b]quinazolin-1-ones has been developed via a multicomponent reaction, which involves the condensation of 2-aminobenzimidazole, dimedone and various aldehydes using chitosan-supported metal nanocomposite as a green, reusable and environmentally benign catalyst system. Environmental friendly, recyclability, cost-effectiveness, easy workup and excellent yields are the major attributes of this one-pot procedure.

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Synthesis and characterization of silica‐coated Fe₃O₄ nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one‐pot synthesis of tetrahydrobenzimidazo[2,1‐b]quinazolin‐1(2H)‐ones

Moussa

Rahmati

2020

Applied Organom Chemis

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In this study, silica-coated Fe 3 O 4 nanoparticle@silylpropyl triethylammonium polyoxometalate catalyst was fabricated and characterized using atomic absorption, inductively coupled plasma optical emission spectrometry, elemental analysis, thermogravimetric analysis, Fourier-transform infrared, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and vibrating sample magnetometry analyses. The activity of this catalyst was examined in the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones. The bonding of the polyoxometalate to the surface of the nanoparticles exhibited excellent catalytic activity in this synthesis. Besides, the catalyst showed good reusability and recovery from the reaction mixture. Tetrahydrobenzimidazo[2,1-b]quinazolin-1 (2H)-ones were synthesized in high yields in the presence of inexpensive supported solid acid catalysts under classical heating conditions.

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Cyclocondensation of 2-Aminobenzimidazole with Dimedone and Its Arylidene Derivatives

Cited by 41 publications

References 0 publications

Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

A three-component one-pot procedure for the synthesis benzimidazolo-quinazolinone derivatives in the presence of chitosan-supported metal nanocomposite as a green and reusable catalyst

Synthesis and characterization of silica‐coated Fe₃O₄ nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one‐pot synthesis of tetrahydrobenzimidazo[2,1‐b]quinazolin‐1(2H)‐ones

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Cyclocondensation of 2-Aminobenzimidazole with Dimedone and Its Arylidene Derivatives

Cited by 41 publications

References 0 publications

Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans

A three-component one-pot procedure for the synthesis benzimidazolo-quinazolinone derivatives in the presence of chitosan-supported metal nanocomposite as a green and reusable catalyst

Synthesis and characterization of silica‐coated Fe3O4 nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one‐pot synthesis of tetrahydrobenzimidazo[2,1‐b]quinazolin‐1(2H)‐ones

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Synthesis and characterization of silica‐coated Fe₃O₄ nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one‐pot synthesis of tetrahydrobenzimidazo[2,1‐b]quinazolin‐1(2H)‐ones