Saturated and unsaturated lactones

Collins, Ian

doi:10.1039/co9960300295

Cited by 25 publications

(9 citation statements)

References 14 publications

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Section: Short Communicationsmentioning

confidence: 99%

“…One of the most general and convenient methods of synthesis of functionally substituted furan-2(5H)-ones is based on reactions of α-hydroxy ketones with compounds containing an activated methylene group [6][7][8].In continuation of our studies in this field, in the present communication we report on the synthesis and chemical transformations of a new class of compounds, 2,5-dihydrofuran-2-imines based on readily accessible α-hydroxy ketones. We found that, contrary to published data [9], tertiary α-hydroxy ketones react with malononitrile to give mixtures of the corresponding 2,5-dihydrofuran-2-imines I and products of their subsequent reaction with the second malononitrile molecule, 2-(2,5-dihydrofuran-2-ylidene)malononitriles II, which were formed in good yields.…”

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confidence: 95%

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Synthesis of new 2-substituted 2,5-dihydrofuranone derivatives and their chemical transformations

Avetisyan¹,

Alvandzhyan²,

Avetisyan³

2009

Russ J Org Chem

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SHORT COMMUNICATIONS2,5-Dihydrofuran-2-ones having functional substituents in the 3-position constitute structural fragments of many natural and synthetic biologically active compounds [1][2][3][4][5]. One of the most general and convenient methods of synthesis of functionally substituted furan-2(5H)-ones is based on reactions of α-hydroxy ketones with compounds containing an activated methylene group [6][7][8].In continuation of our studies in this field, in the present communication we report on the synthesis and chemical transformations of a new class of compounds, 2,5-dihydrofuran-2-imines based on readily accessible α-hydroxy ketones. We found that, contrary to published data [9], tertiary α-hydroxy ketones react with malononitrile to give mixtures of the corresponding 2,5-dihydrofuran-2-imines I and products of their subsequent reaction with the second malononitrile molecule, 2-(2,5-dihydrofuran-2-ylidene)malononitriles II, which were formed in good yields. Detailed examination of this reaction with a view to find optimal conditions showed that the process occurs even in the absence of a catalyst upon mixing of the reactants in alcohol or benzene.General procedures for the reactions of α-hydroxy ketones with malononitrile. a. The corresponding α-hydroxy ketone and malononitrile, 50 mmol each, were added to a solution of 0.115 g (5 mmol) of metallic sodium in 25 ml of anhydrous ethanol. The mixture was kept for 15-20 h at room temperature, the solvent was distilled off under reduced pressure, the residue was dissolved in benzene, and the precipitate was filtered off and recrystallized from ethanol-water (2 : 1) to isolate compound IIa or IIb. The benzene solution was diluted with four volumes of hexane, and the precipitate was filtered off and recrystallized from heptane. We thus isolated compound Ia or Ib.b. A mixture of 50 mmol of α-hydroxy ketone and 50 mmol of malononitrile in 25 ml of anhydrous ethanol was kept for 15-20 h at room temperature. The mixture was then treated as described above in a. c. A mixture of 50 mmol of α-hydroxy ketone and 50 mmol of malononitrile in 25 ml of anhydrous benzene was kept for 15-20 h at room temperature. The solvent was partially distilled off under reduced pressure, and the mixture was then treated as described above in a. 2-Imino-4,5,5-trimethyl-2,5-dihydrofuran-3-carbonitrile (Ia). Yield 43 (a), 25 (b), 55% (c); mp 97-98°C (oily substance [10]). IR spectrum, ν, cm -1 : 2230 (CN), 1665 (C=N), 1075 (C-O-C), 985 (CH), 890 (CH). 1 H NMR spectrum, δ, ppm: 1.4 s (6H, CH 3 ), 2.20 s (3H, CH 3 ), 6.45 s (1H, NH). Found, %: C 64.01; H 6.48; N 19.01. C 8 H 10 N 2 O. Calculated, %: C 63.98; H 6.71; N 18.65.2-Imino-4-methyl-5,5-pentamethylene-2,5-dihydrofuran-3-carbonitrile (Ib). Yield 38 (a), 17 (b), 60% (c); mp 89-90°C. IR spectrum, ν, cm -1 : 2225 R 1 = R 2 = Me (a), R 1 R 2 = (CH 2 ) 5 (b).

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Section: Short Communicationsmentioning

confidence: 99%

mentioning

confidence: 95%

Synthesis of new 2-substituted 2,5-dihydrofuranone derivatives and their chemical transformations

Avetisyan¹,

Alvandzhyan²,

Avetisyan³

2009

Russ J Org Chem

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“…Moreover, it is present in a variety of biologically active compounds such as vitamin C and digitoxin [182]. The substituted furanone 1 1 1 was conveniently synthesized in a single-mode microwave oven by irradiation of an ethanolic solution of 3-hydroxy-3-methyl-2-butanone 110 with ethylcyanoacetate, in the presence of sodium ethoxide (Fig.…”

Section: Furanonesmentioning

confidence: 99%

Recent Advances in Microwave-Assisted Synthesis of Heterocyclic Compounds

Molteni¹,

Ellis²

2005

COS

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“…Thus, there has been a continuous interest in the development of efficient and convenient methods for the preparation of these heterocycles and in their applications [11][12][13][14][15][21][22][23]. One of the most convenient and common methods of synthesis of functionalized 2,5-dihydro-2-oxofurans is the condensation of a-hydroxyketones with compounds containing active methylene groups (dimethyl malonate, ethyl cyanoacetate, ethyl acetoacetate) in basic conditions [20,24,25].…”

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confidence: 99%

“…Introduction 2,5-Dihydro-2-oxofuran derivatives are a large family of heterocycles that include synthetically useful compounds, several natural products [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15], and a number of drugs with diverse biological activities such as antifungal, antibacterial, and anti-inflammatory properties [16][17][18][19][20]. Thus, there has been a continuous interest in the development of efficient and convenient methods for the preparation of these heterocycles and in their applications [11][12][13][14][15][21][22][23].…”

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confidence: 99%