2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

Gajdoš, Peter; Pavlíková, Soňa; Bureš, Filip; Krutošíková, A.

doi:10.2478/bf02475999

Cited by 5 publications

(8 citation statements)

References 22 publications

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“…16,17 The second method involves the cyclisation of N-thioacyl-α-aminoester with hydrazine. 18 The title compounds 5 are well accessible 16,19 from methyl 4H-furo[3,2-b]pyrrole-5-carboxylate 1 via its transformation to carbohydrazide 2. Hydrazinolysis was achieved in 80% yield by heating of 1 with hydrazine hydrate in ethanol for 20h 16 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives and their antibacterial activity

Zemanov¹,

Gaparov²,

Kraic³

et al. 2017

Arkivoc

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Furo [2',3':4,5]pyrrolo [1,2-d][1,2,4]triazin-8(7H)-ones 5 were synthesized either by reaction of carbohydrazide 2 with triethyl orthoesters or by acetylation of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate 1 followed by thionation of 4-acetylfuro[3,2-b]pyrrole-5-carboxylate 3 and cyclisation of thione 4 with hydrazine. Triazine 5a afforded the corresponding thione 7 by reaction with P2S5. Upon reaction with alkyl-or acylhalogenides compounds 5 and 7 gave N(7)-substituted products 6 and 8, respectively. Finally, triazino-triazinone derivative 9 was synthesized by cyclisation of thione 8b with hydrazine. Compounds 5 -9 were evaluated for their antibacterial activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis of furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives and their antibacterial activity

Zemanov¹,

Gaparov²,

Kraic³

et al. 2017

Arkivoc

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“…Carboxhydrazides 1a,b were routinely prepared by condensation of 5-[(3-trifluoromethyl)phenyl]furan-2-carboxaldehyde [16] with methyl azidoacetate in methanol in the presence of sodium methoxide giving methyl 2-azido-3-{5-[3-(trifluoromethyl)phenyl]-2-furyl} propenoate, which underwent the cyclization in boiling toluene to give methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate [17]. Carboxhydrazide 1a was formed in 88% yield by the reaction of carboxylate with hydrazine-hydrate in ethanol.…”

Section: Resultsmentioning

confidence: 99%

“…Carboxhydrazide 1a was formed in 88% yield by the reaction of carboxylate with hydrazine-hydrate in ethanol. Carboxhydrazide 1b was obtained in 67% yield by alkylation of carboxylate with benzyl bromide in benzene-aqueous sodium hydroxide solution in the presence of benzyltriethylammonium chloride and subsequent hydrazinolysis [17].…”

Section: Resultsmentioning

confidence: 99%

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Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides

2008

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“…Compound 5 belongs to α,β-unsaturated ketones (chalcones), which were in the past the subject of our study [22]. The 1 H NMR spectrum of compound 5 displays doublets for double bond protons at 7.61 ppm for H-12 and 7.52 ppm for H-13.…”

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confidence: 99%

Reactions of 5-[3-(trifluoromethyl)-phenyl]furan-2-carbaldehyde

Gajdoš

Miklovič

Krutošíková

2006

Chem Heterocycl Compd

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Keywords: methyl 2-[3-(trifluoromethyl)phenyl)]-4H-furo[3,2-b]pyrrole-5-carboxylate, 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde, 2-[3-(trifluoromethyl)phenyl)]furo[3,2-c]pyridine, Knoevenagel reaction.During the past few decades many results have been published in the field of synthesis and study of physical and chemical properties of heterocyclic compounds containing a furan ring connected or fused with a benzene ring or with different heterocyclic systems.Substituted furans are ubiquitous structural units in natural products and pharmaceuticals [1] and have been widely used as synthetic intermediates [2,3]. Many of the published condensation products are biologically active compounds [4,5] or can be used as intermediates in organic synthesis [6][7][8][9].In the past two decades one of us was interested in the syntheses, reaction, and aromaticity of variously substituted furo[3,2-b]pyrroles and their [2,3-b]-isomers [10,11]. Substitution, addition, and cycloaddition reactions of furo[3,2-b]pyrroles and their condensed derivatives involving the interesting transformations of furo[3,2-b]pyrrole system were presented. We also reported on the synthesis of 2-arylfuro[3,2-c]pyridines [12, 13] and 2,3-dimethylfuro[3,2-c]pyridine [14]. Later on some furo[3,2-c]pyridines have been used for the preparation of Cu(II) and Ni(II) complexes [15]. Furo[3,2-c]pyridine and its 2-methyl-, 2,3-dimethyl-and benzo [4,5] derivative were used for the first time as ligands to synthesize potentially new Werner clathrates, and the structural characterization, spectral, and magnetic properties of isothiocyanate nickel(II) complexes were published [16,17].

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2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

Cited by 5 publications

References 22 publications

Synthesis of furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives and their antibacterial activity

Synthesis of furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives and their antibacterial activity

Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides

Reactions of 5-[3-(trifluoromethyl)-phenyl]furan-2-carbaldehyde

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