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Journal articles on the topic '5]furo(2'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Sleziak, Róbert, Slávka Balážiová, and Alžbeta Krutošíková. "Reactions of Furo[2,3-b]pyrrole and Furo[3,2-b]pyrrole-Type Aldehydes." Collection of Czechoslovak Chemical Communications 64, no. 7 (1999): 1135–46. http://dx.doi.org/10.1135/cccc19991135.

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The synthesis of methyl 2-formyl-6-(methoxymethyl)furo[2,3-b]pyrrole-5-carboxylate (1d) is described. The reactions of methyl 2-formylfuro[2,3-b]pyrrole-5-carboxylates 1a-1d with malononitrile afforded methyl 2-(2,2-dicyanovinyl)furo[2,3-b]pyrrole-5-carboxylates 3a-3d, with methyl cyanoacetate methyl 2-[2-cyano-2-(methoxycarbonyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 4a-4d and with 2-furylacetonitrile methyl 2-[2-cyano-2-(2-furyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 5a-5d. Compounds 1b-1d and methyl azidoacetate gave the appropriate vinylazides 6b-6d, which were used for preparation of su

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2

Zemanová, Ivana, and Renata Gašparová. "SYNTHESIS AND REACTIONS OF NEW DERIVATIVES OF FURO[3,2-b]PYRROLE." Nova Biotechnologica et Chimica 12, no. 2 (2013): 100–107. http://dx.doi.org/10.2478/nbec-2013-0012.

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Abstract Synthesis of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate is taken place in two step synthesis. Vilsmeier-Haack reaction of 4H-furo[3,2-b]pyrrole-5-carboxylate 1 led to methyl 2-formyl-4H-furo[3,2- b]pyrrole-5-carboxylate 4, which served as starting compound for synthesis of furo[3,2-b]pyrrole-2- aldoxime 5 and methyl 2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-4H-furo[3,2-b]pyrrole-5- carboxylate 7. The hydrazinolysis of 1 was prepared by carbohydrazide 2, which subsequently reacted with aldehydes to form of derivatives 3. Pyrazole derivatives 11 were prepared by the reaction

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3

Janeba, Zlatko, Noha Maklad, and Morris J. Robins. "Synthesis of 6-(alkoxymethyl)- and 6-(alkylsulfanylmethyl)furo[2,3-d]pyrimidin-2(3H)-one analogues." Canadian Journal of Chemistry 84, no. 4 (2006): 561–68. http://dx.doi.org/10.1139/v06-042.

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Treatment of 6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one (2) with 1-iodoalkanes and potassium carbonate resulted in predominant formation of N3 (and minor amounts of O2) alkylated regioisomers. Treatment of the 3-alkyl products (3) with thionyl chloride gave highly reactive 6-chloromethyl intermediates (5). Direct solvolysis of 5 in alcohol solutions (~50 °C) produced 3-alkyl-6-(alkoxymethyl)furopyrimidin-2(3H)-ones (6), whereas extensive decomposition of 5 occurred with added base promoters. Sonication of 5 with sodium thioacetate in acetonitrile gave the air-stable 6-(alkylsulfanylmethyl

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4

K., C. MAJUMDAR, and DAS U. "Studies on Sigmatropic Rearrangements : Regioselective Synthesis of Coumarins, Quinolones and Thiocoumarins with 3,4-Fused Pyran or Furan Ring Systems by Claisen Rearrangement." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 884–90. https://doi.org/10.5281/zenodo.5900433.

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Department of Chemistry, University of Kalyam, Kalyana-741 235 <em>Manuscript received 4 September 1997</em> A brief review of the regioselective synthesis of pyrano[3,2-<em>c</em>][1]benzopyran-5(2<em>H</em>)-ones, pyrano[3,2-<em>c</em>][1]benzothiapyran-5(2<em>H</em>)-one, pyrano[3,2-<em>c</em>]quinolin-5(2<em>H</em>)-ones, pyrano(2,3-<em>c</em>)[1]benzopyran-5(3<em>H</em>)-ones, 3<em>H</em>-pyrano[2,3-<em>c</em>)quinolin-5(6H)-ones, thiapyrano(2, 3- b) (1)benzothiapyran-5(2<em>H</em>)-ones, thiapyrano[2,3-<em>b]</em> [1]benzopyran-5(2<em>H</em>)-ones, furo[3,2-<em>c</em>] [1] benzopyra

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5

Kraľovičová, Eva, Alžbeta Krutošíková, and Jaroslav Kováč. "Preparation and reactions of thieno[3,2-b]furan derivatives." Collection of Czechoslovak Chemical Communications 51, no. 8 (1986): 1685–91. http://dx.doi.org/10.1135/cccc19861685.

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Reactions of 3-(5-aryl-2-furyl)propenoic, 3-(2-benzo[b]furyl)propenoic and 3-(5-ethoxycarbonyl-4H-furo[3,2-b]-2-pyrrolyl)propenoic acids with thionyl chloride in the presence of triethylbenzylammonium chloride were investigated. The obtained 2-arylthieno[3,2-b]-furan-5-carboxylic acid chlorides Ia - Ic and 3-chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride afforded in substitution nucleophilic reactions the corresponding esters V and carboxylic acids VI which were decarboxylated to VII. 3-Chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride (Id), 6-ethoxycarbonyl-3-chlorothie

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6

Gajdoš, Peter, Soňa Pavlíková, Filip Bureš, and Alžbeta Krutošíková. "2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions." Open Chemistry 3, no. 2 (2005): 311–25. http://dx.doi.org/10.2478/bf02475999.

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AbstractThe synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By

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7

Yang, Ru Chun, Hui Zhu, Xuan Ye Jin, Qiang Xiao, and Yong Ju. "Synthesis of Bicyclic Furo[2,3-d]pyrimidine Deoxynucleosides Conjugated with N-Diisopropylphosphoryl Amino Acids." Advanced Materials Research 881-883 (January 2014): 405–9. http://dx.doi.org/10.4028/www.scientific.net/amr.881-883.405.

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A series of bicyclic furo[2,3-d]pyrimidine nucleosides conjugated with N-diisopropylphosphoryl amino acids were synthesized from 2′-deoxy-5-iodouridine. The key step is its cross coupling with the 5-phthalimido-1-pentyne under Sonogashira reaction condition. 5-Endo-dig electrophilic cyclization catalyzed by AgNO3 is used to afford the furo[2,3-d]pyrimidines.

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8

Abu-Hashem, Ameen Ali, and Sami A. Al-Hussain. "The Synthesis, Antimicrobial Activity, and Molecular Docking of New 1, 2, 4-Triazole, 1, 2, 4-Triazepine, Quinoline, and Pyrimidine Scaffolds Condensed to Naturally Occurring Furochromones." Pharmaceuticals 15, no. 10 (2022): 1232. http://dx.doi.org/10.3390/ph15101232.

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This study aims to synthesize a new series of furochromone derivatives, evaluate their antimicrobial properties, and improve the permeability of potent compounds to inhibit different types of bacteria and fungi. Hence, Substituted furo[3,2-g]chromene-6-carbonitrile (3a,b) readily form 7-amino-5-methyl-furo [3,2-g]chromene-6-carbonitrile (4a,b) via reduction using sodium borohydride in methanol. The same compounds of (4a,b) were used as starting materials for the synthesis of new furochromone derivatives such as furochromeno [2,3-d]pyrimidines, N- (6-cyano- 5-methyl-furochromene) acetamide, N-(

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9

Mehta, Vaibhav P., Sachin G. Modha, Denis Ermolat'ev, Kristof Van Hecke, Luc Van Meervelt, and Erik V. Van der Eycken. "Diversity-Oriented Synthesis of Substituted Furo[2,3-b]pyrazines." Australian Journal of Chemistry 62, no. 1 (2009): 27. http://dx.doi.org/10.1071/ch08376.

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A highly efficient method for the synthesis of diversely substituted furo[2,3-b]pyrazines has been elaborated. The Ag+- or iodine-mediated electrophilic cyclization of readily generated 5-chloro-3-substituted ethynyl-1-(4-methoxybenzyl)-pyrazin-2(1H)-ones affords substituted furo[2,3-b]pyrazines, which undergo various palladium catalyzed reactions to generate a library of difficult to attain diversely substituted furo[2,3-b]pyrazines.

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10

El-Sayed, K., A. M. Abd El-Rahman, and H. L. Ammon. "Visnagin, C13H10O4(5-methoxy-2-methyl-furo-(9)-chromen)." Acta Crystallographica Section A Foundations of Crystallography 43, a1 (1987): C55. http://dx.doi.org/10.1107/s0108767387084009.

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11

Krutošíková, Alžbeta, Miloslava Dandárová, and Vladimír Bobošík. "Derivatives of Furo[3,2-b]pyrrole." Collection of Czechoslovak Chemical Communications 59, no. 2 (1994): 473–81. http://dx.doi.org/10.1135/cccc19940473.

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A number of methyl 2-substituted, 2,3-disubstituted-4H-furo[3,2-b]pyrrole-5-carboxylates (V - VII) and methyl 1H-benzo[b]furo[3,2-b]pyrrole-2-carboxylate (VIII) was prepared by the thermolysis of corresponding methyl 2-azido-3-(R1,R2-substituted-2-furyl)propenoates (I - IV). N-Methyl and N-benzyl derivatives IX - XVI were prepared at the phase-transfer catalysis conditions. Hydrolysis of some N-methyl and N-benzyl substituted esters furnished corresponding acids XVII - XXII. The hydrazides XXIII - XXX were obtained from corresponding esters and hydrazine hydrate. The preparation of 1-benzylben

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12

Vadla, Balakishan, and Sailu Betala. "Novel 1,2,3-Triazole-functionalized pyrido[3',2':4,5]furo[3,2-d]pyrimidin- 4(3H)-one Derivatives: Synthesis, Anticancer Activity, CoMFA and CoMSIA Studies." Letters in Organic Chemistry 17, no. 12 (2020): 969–78. http://dx.doi.org/10.2174/1570178617666200319124017.

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A series of novel triazole functionalized pyrido [3',2':4,5] furo[3,2-d] pyrimidin-4 (3H)-one derivatives 7a-p were prepared from ethyl furo[2,3-b]pyridine-2-carboxylate 3 on reaction with ammonia to afford furo[2,3-b]pyridine-2-carboxamide 4. This compound, on reaction with triethyl orthoformate TEOF, gave compound 5. Compound 5 on propargylation, followed by a reaction with substituted aryl azides under Sharpless reaction conditions, furnished triazole tagged pyrido [3',2':4,5]furo[3,2-d] pyrimidin-4(3H)-one derivatives. All the products 7a-p were screened against four human cancer cell line

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13

Krutošíková, Alžbeta, and Mikuláš Hanes. "Substituted 4-Benzylfuro[3,2-b]pyrroles." Collection of Czechoslovak Chemical Communications 57, no. 7 (1992): 1487–94. http://dx.doi.org/10.1135/cccc19921487.

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Preparation of 4-benzylfuro[3,2-b]pyrroles is described and their reactions with selected dienophiles are discussed. Utilization of 4-acetylfuro[3,2-b]pyrroles for preparation of 4-substituted derivatives of furo[3,2-b]pyrrole and the synthesis of ethyl 4-(2- and 4-nitrobenzyl)furo[3,2-b]pyrrole-5-carboxylates for fusing to a 1,4-diazepine system is presented.

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14

Zhou, Rong, Yanli Ding, and Mili Yang. "Synthesis of 2-Substituted Benzo[b]furans/furo-Pyridines Catalyzed by NiCl2." Catalysts 9, no. 12 (2019): 1019. http://dx.doi.org/10.3390/catal9121019.

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The first Ni-catalyzed tandem synthesis of 2-substituted benzo[b]furans/furo-pyridines from 2-halophenols and 1-alkynes was explored under Cu-free and phosphine-free conditions. The protocol was carried out with NiCl2/5-nitro-1, 10-phenanthroline in DMA (N,N-dimethylacetamide) at 120 °C. It was found to be simple, cost effective, and have a wide substrate scope. Additionally, the method is compatible with heteroaryl substrates, resulting in the formation of 2-substituted benzo[b]furans/furo-pyridines in reasonable to good yields.

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15

Uher, Michal, Ján Leško, and Ivan Tóth. "Furo[2,3-d]thiazoles." Collection of Czechoslovak Chemical Communications 51, no. 8 (1986): 1678–84. http://dx.doi.org/10.1135/cccc19861678.

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Carbonyl isothiocyanates react with 5-amino-2-furancarboxylates to give the corresponding acylthioureas which cyclize to condensed derivatives related to furo[2,3-d]thiazoles. Structure of these substances was corroborated by IR, mass, 1H and 13C{1H}NMR spectral means.

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16

Canonne, P., and M. Belley. "Étude de l'action des organomagnésiens sur les dérivés carboxyliques de la pyridine." Canadian Journal of Chemistry 65, no. 8 (1987): 1885–90. http://dx.doi.org/10.1139/v87-316.

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Reactions of Grignard reagents with pyridinecarboxylic esters 1, 2, pyridine-2-carboxylic acid (3), and 2,3-pyridinedicarboxylic acid anhydride (5) show regioselectivity at the carbonyl in position 2. This is exemplified by an efficient synthesis of 7,7-dialkylated-7H-furo[3,4-b]-substituted pyridin-5-ones.

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17

Sleziak, Róbert, and Alžbeta Krutošíková. "Cycloaddition Reactions of Furo[2,3-b]pyrroles." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 321–28. http://dx.doi.org/10.1135/cccc19990321.

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Reactions of furo[2,3-b]pyrroles with dimethyl butynedioate and ethyl propynoate were investigated. The reaction course is influenced by the substituents on the fused system. Products of [4+2]cycloaddition to the furan ring leading to indole derivatives have been observed. In the case of the reaction of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (1a) with dimethyl butynedioate, products of [4+2]cycloaddition to the furan ring as well as of Michael addition to the pyrrole ring leading to N-substituted indole derivative 3 have been observed.

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18

Krutošíková, Alžbeta, Slavomír Mastik, Miloslava Dandárová, and Antonín Lyčka. "Synthesis and Reactions of 8-Hydrazinofuro[2',3':4,5]pyrrolo-[1,2-d][1,2,4]triazines." Collection of Czechoslovak Chemical Communications 62, no. 10 (1997): 1612–22. http://dx.doi.org/10.1135/cccc19971612.

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5-Ethyl-8-hydrazinofuro[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazine (4a) and its 2-methyl derivative 4b were prepared from 4H-furo[3,2-b]pyrrole-5-carbohydrazides 1a and 1b, respectively. Compounds 1a and 1b reacted with triethyl orthopropionate to give 2a and 2b which afforded with phosphorus(V) sulfide corresponding thiones 3a and 3b. The title compounds 4a and 4b were made by treatment of 3a and 3b with hydrazine hydrate. By reactions of triethyl orthoesters with the title compounds and similar derivatives furo[2'3':4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 5a-5j were prepared. R

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19

Janeba, Zlatko, Jan Balzarini, Graciela Andrei, Robert Snoeck, Erik De Clercq, and Morris J. Robins. "Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(p-toluenesulfonyl)uracil derivatives." Canadian Journal of Chemistry 84, no. 4 (2006): 580–86. http://dx.doi.org/10.1139/v06-041.

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Sonogashira coupling of 5-iodouracil (2) and trimethylsilylacetylene gave 5-(trimethylsilylethynyl)uracil (3), which was deprotected to give 5-ethynyluracil (4). Copper(I)-catalyzed cyclization of 4 gave furo[2,3-d]pyrimidin-2(3H)-one (5). Tosylation of 2 and 4 gave the 1-(p-toluenesulfonyl) derivatives 6 and 7, respectively. The tosylated compound 6 and trimethylsilylacetylene did not undergo Sonogashira coupling, and copper(I)-catalyzed cyclization of 7 did not occur. Coupling of 2 with several terminal alkynes gave 5-(alkyn-1-yl)uracil derivatives (9), which underwent tosylation to produce

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20

Mphahlele, Malose J., Samantha Gildenhuys, and Emmanuel N. Agbo. "In Vitro Evaluation and Docking Studies of 5-oxo-5H-furo[3,2-g]chromene-6-carbaldehyde Derivatives as Potential Anti-Alzheimer’s Agents." International Journal of Molecular Sciences 20, no. 21 (2019): 5451. http://dx.doi.org/10.3390/ijms20215451.

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A series of novel 2-carbo–substituted 5-oxo-5H-furo[3,2-g]chromene-6-carbaldehydes and their 6-(4-trifluoromethyl)phenylhydrazono derivatives have been prepared and evaluated for biological activity against the human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The most active compounds from each series were, in turn, evaluated against the following enzyme targets involved in Alzheimer’s disease, β-secretase (BACE-1) and lipoxygenase-15 (LOX-15), as well as for anti-oxidant potential. Based on the in vitro results of ChE and β-secretase inhibition, the kinetic studies were con

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21

Vasco, Raquel F. V., Rosa M. A. Moyses, Roberto Zatz, and Rosilene M. Elias. "Furosemide Increases the Risk of Hyperparathyroidism in Chronic Kidney Disease." American Journal of Nephrology 43, no. 6 (2016): 421–30. http://dx.doi.org/10.1159/000446449.

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Background: Diuretics are widely used in patients with chronic kidney disease (CKD). While thiazide-like diuretics limit urinary calcium excretion, loop diuretics (LD) promote calcium wasting, which might facilitate the development of secondary hyperparathyroidism (HPT2). We sought to investigate, in CKD patients not on dialysis, the influence of either hydrochlorothiazide (Hydro) or furosemide (Furo) on circulating parathyroid hormone (PTH) and whether such actions are determined by the effects of these compounds on calcium excretion. Methods: Electronic charts of all nephrology outpatients (

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22

Mphahlele, Malose J., Emmanuel N. Agbo, Samantha Gildenhuys та Itumeleng B. Setshedi. "Exploring Biological Activity of 4-Oxo-4H-furo[2,3-h]chromene Derivatives as Potential Multi-Target-Directed Ligands Inhibiting Cholinesterases, β-Secretase, Cyclooxygenase-2, and Lipoxygenase-5/15". Biomolecules 9, № 11 (2019): 736. http://dx.doi.org/10.3390/biom9110736.

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A series of 5-oxo-5H-furo[3,2-g]chromene-6-carbaldehydes and their hydrazone derivatives were evaluated as potential multi-target-directed ligands in vitro against cholinesterases, β-secretase, cyclooxygenase-2, and lipoxygenase-15 (LOX-15), as well as for free radical-scavenging activities. The most active compounds against LOX-15 were also evaluated for activity against the human lipoxygenase-5 (LOX-5). Kinetic studies against AChE, BChE, and β-secretase (BACE-1) were performed on 2-(3-fluorophenyl)- (3b) and 2-(4-chlorophenyl)-6-[(4-trifluoromethylphenyl)hydrazonomethyl]furo[3,2-h]chromen-5

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23

Zlatoidský, Pavol, Elisa Martinelli, Emil Svensson, and Alexis Pruvost. "A Facile Access to Novel (5+5) Annellated Heterocycles: Synthesis of a Furopyrrole, an Imidazoimidazole and a Pyrroloimidazole." Synthesis 51, no. 18 (2019): 3491–98. http://dx.doi.org/10.1055/s-0039-1689916.

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We describe the synthesis of an ethyl 3-aryl-6H-furo[2,3-b]pyrrole-5-carboxylate 2, a 5-aryl-1H-imidazo[1,2-a]imidazole 3, and an ethyl-1-aryl-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate 4 as new hinge-binding motifs for PI3K kinase inhibitors. A key reaction for the formation of 2 and 4 is the Hemmetsberger–Knittel cyclization of acryloazides. The core of 3 is accessible through reaction of an α-haloketone with 2-aminoimidazole.

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24

Gašparová, Renata, Ján Titiš, and Filip Kraic. "Synthesis of Furo[3,2-b]pyrrole-5-carboxhydrazides and Their Cu, CO and Ni Complexes." Scientific World Journal 2012 (2012): 1–4. http://dx.doi.org/10.1100/2012/915798.

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Carboxhydrazides3were synthesized by reaction of substituted furo[3,2-b]pyrrole-5-carboxhydrazides1with 4-oxo-4H-chromene-2-carboxaldehyde2in the presence of 3-methyl-benzenesulfonic acid in ethanol. Carboxhydrazides3were used as ligands for synthesis of Cu, Co, and Ni complexes4.

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25

Ashok, D., E. V. L. Madhuri, M. Sarasija, et al. "Synthesis, biological evaluation and molecular docking of spirofurochromanone derivatives as anti-inflammatory and antioxidant agents." RSC Advances 7, no. 41 (2017): 25710–24. http://dx.doi.org/10.1039/c7ra01550j.

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A series of 2′-substituted-3′-methylspiro[cyclohexane-1,7′-furo[3,2-g]chroman]-5′(7′H)-one, 5a–i and 7a–u have been synthesized using an eco-friendly approach with good anti-inflammatory and antioxidant activity.

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26

Kraľovičová, Eva, Alžbeta Krutošíková, Jaroslav Kováč, and Miloslava Dandárová. "Electrophilic substitution reactions of furo[3,2-b]pyrrole derivatives." Collection of Czechoslovak Chemical Communications 51, no. 1 (1986): 106–11. http://dx.doi.org/10.1135/cccc19860106.

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Formylation of ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate and its N-methyl analogue afforded the 2-formyl products Ia,b which on nitration yielded 2-nitro derivatives IIc,d. Formylation, nitration, Mannich reaction, and copulation of the starting products, having position 2 occupied by an aryl, took place at the pyrrole ring.

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27

Ahn, Dae-Gyun, Gun Young Yoon, Sunhee Lee, et al. "A Novel Frameshifting Inhibitor Having Antiviral Activity against Zoonotic Coronaviruses." Viruses 13, no. 8 (2021): 1639. http://dx.doi.org/10.3390/v13081639.

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Recent outbreaks of zoonotic coronaviruses, such as Middle East respiratory syndrome coronavirus (MERS-CoV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), have caused tremendous casualties and great economic shock. Although some repurposed drugs have shown potential therapeutic efficacy in clinical trials, specific therapeutic agents targeting coronaviruses have not yet been developed. During coronavirus replication, a replicase gene cluster, including RNA-dependent RNA polymerase (RdRp), is alternatively translated via a process called -1 programmed ribosomal frameshift (−1

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28

Magotra, D. K., V. K. Gupta, Rajnikant, K. N. Goswami, and B. D. Gupta. "5-Acetoxy-6-(1,1-dimethyl-2-propenyl)-2H-furo[2,3-h][1]benzopyran-2-one." Acta Crystallographica Section C Crystal Structure Communications 51, no. 12 (1995): 2637–39. http://dx.doi.org/10.1107/s0108270195008353.

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29

Harada, Kazuho, Kuniaki Sasaki, Eisuke Kaji, and Shonosuke Zen. "An One-Pot Synthesis of 5,11-Ethenoisoxazolo[5''',4''':3',4']furo[2'',3'':7',8']naphtho[2',3':4,5]furo[3,4-d]isoxazoles from 2-Isoxazoline-2-oxides." HETEROCYCLES 36, no. 2 (1993): 253. http://dx.doi.org/10.3987/com-92-6234.

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30

Tumkevicius, Sigitas, Viktoras Masevicius, and Grazina Petraityte. "4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines." Synthesis 44, no. 09 (2012): 1329–38. http://dx.doi.org/10.1055/s-0031-1290524.

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31

Fournet, Alain, Beatrice Vagneur, Pascal Richomme, and Jean Bruneton. "Aryl-2 et alkyl-2 quinoléines nouvelles isolées d'une Rutacée bolivienne: Galipealongiflora." Canadian Journal of Chemistry 67, no. 12 (1989): 2116–18. http://dx.doi.org/10.1139/v89-329.

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Five new 2-aryl and 2-alkyl quinoline alkaloids were obtained from Galipeallongiflora Krause (Rutaceae). These are 2-phenylquinoline 1, 2-(3′,4′-methylenedioxyphenethyl)quinoline 2, 2-(3′,4′-dimethoxyphenethyl)quinoline 3, 2-(3′,4′-methylenedioxystyryl)-4-methoxyquinoline 4, and 2-(1′,2′-pentenyl)-4-methoxyquinoline 6. They are accompanied by three known 2-substituted quinolines, 2-n-amyl-4-methoxyquinoline 5, 2-(3′4′-methylenedioxyphenethyl)-4-methoxyquinoline 7, and 2-phenyl-4-methoxyquinoline 8, and by two known furo[2,3b]quinoline alkaloids: evolitrine and skimmianine. Keywords: Galipealon

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32

Gašparová, Renata, Margita Lácová, and Alžbeta Krutošíková. "Reactions of Substituted Furo[3,2-b]pyrrole-5-carbohydrazides Under Classical and Microwave Conditions." Collection of Czechoslovak Chemical Communications 70, no. 12 (2005): 2101–11. http://dx.doi.org/10.1135/cccc20052101.

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Substituted hydrazones 5 and 6 were synthesized by the reaction of the corresponding furo[3,2-b]pyrrole-5-carboxyhydrazides 1 with 6-substituted 4-oxochromene-3-carbaldehydes 2 and methyl 2-formylfuro[3,2-b]pyrrole-5-carboxylates 3 under microwave irradiation as well as by the classical method. The beneficial effect of the microwave irradiation on these reactions was a shortening of the reaction time and an increase in the yields. The reactions of 1 with 4-[(4-oxochromen-3-yl)methylidene]-2-phenyloxazol-5(4H)-one (4) were also studied. Compounds 7 or 8 were obtained, depending on the reaction

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33

Gašparová, Renáta, Martin Moncman, and Branislav Horváth. "Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides." Open Chemistry 6, no. 2 (2008): 180–87. http://dx.doi.org/10.2478/s11532-008-0009-4.

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AbstractThe effect of microwave irradiation on the reactions of 2-[3-(trifluoromethyl)phenyl]-4-R1-furo[3,2-b]pyrrole-5-carboxhydrazides 1 with 5-arylfuran-2-carboxaldehydes 2, thiophene-2-carboxaldehyde (3) and methyl 2-formylfuro[3,2-b]pyrrole-5-carboxylates 4 has been studied. Reactions of 1 with formic and acetic acid, respectively, led to acylhydrazides 9a–c. Reaction of 1a with 4-substituted 1,3-oxazol-5(4H)-one 10 led to imidazole derivative 13. 1,2,4-Triazole-3-thiones 15a,b were synthesized by two-step reaction of 1a with potassium isothiocyanate and phenyl isothiocyanate, respectivel

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34

GaOpen Chemistry 3, no. 4 (2005): 622–46. http://dx.doi.org/10.2478/bf02475192.

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AbstractThe reactions of substituted furo[3,2-b]pyrrole-5-carboxhydrazides 1 with 5-arylfuran-2-carboxaldehydes 2, 4,5-disubstituted furan-2-carboxaldehydes 3 and thiophene-2-carboxaldehyde 4 has been studied. The advantage of microwave irradiation on some of these reactions was reflected in the reduced reaction time and increased yields. Reactions of 1 with 4-substituted 1,3-oxazol-5(4H)-ones 11 led to diacylhydrazines 13 or to imidazole derivatives 14 depending on the temperature. 1,2,4-Triazole-3-thione 17 was synthesized by two-step reaction of 1 with phenylisothiocyanate and subsequent ba

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35

Delettré, J., M. E. Delaitre, P. Vigny, and J. Moron. "Structure du méthyl-7 5H-furo[3',2':6,7]chroméno[3,4-c]pyridinone-5." Acta Crystallographica Section C Crystal Structure Communications 42, no. 12 (1986): 1851–53. http://dx.doi.org/10.1107/s0108270186090297.

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36

Masevicius, Viktoras, Grazina Petraityte, and Sigitas Tumkevicius. "ChemInform Abstract: 4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines." ChemInform 43, no. 35 (2012): no. http://dx.doi.org/10.1002/chin.201235184.

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37

Thunhorst, R. L., Z. Xu, M. Z. Cicha, A. M. Zardetto-Smith, and A. K. Johnson. "Fos expression in rat brain during depletion-induced thirst and salt appetite." American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 274, no. 6 (1998): R1807—R1814. http://dx.doi.org/10.1152/ajpregu.1998.274.6.r1807.

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The expression of Fos protein (Fos immunoreactivity, Fos-ir) was mapped in the brain of rats subjected to an angiotensin-dependent model of thirst and salt appetite. The physiological state associated with water and sodium ingestion was produced by the concurrent subcutaneous administration of the diuretic furosemide (10 mg/kg) and a low dose of the angiotensin-converting enzyme (ACE) inhibitor captopril (5 mg/kg; Furo/Cap treatment). The animals were killed 2 h posttreatment, and the brains were processed for Fos-ir to assess neural activation. Furo/Cap treatment significantly increased Fos-i

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38

Horak, Yuriy I., Roman Z. Lytvyn, Andrii R. Vakhula, Yuriy V. Homza, Nazariy T. Pokhodylo, and Mykola D. Obushak. "New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives." Beilstein Journal of Organic Chemistry 21 (February 26, 2025): 444–50. https://doi.org/10.3762/bjoc.21.31.

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A new tandem sequence involving the Ugi reaction and Diels–Alder [4 + 2] cycloaddition based on vinylfuran and 1,3-butadienylfuran derivatives was designed and studied. It was found that in the case of 3-(furan-2-yl)acrylaldehyde, a one-pot Ugi reaction and intramolecular Diels–Alder vinylarene (IMDAV) reaction leads to the formation of the insufficiently studied furo[2,3-f]isoindole derivatives. Ugi adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, and an amine spontaneously underwent the IMDAV reaction with a high level of stereoselectivity, leading to

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39

Zemanová, Ivana, and Renata Gašparová. "NMR spectroscopic properties of furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives." Nova Biotechnologica et Chimica 16, no. 2 (2017): 147–51. http://dx.doi.org/10.1515/nbec-2017-0020.

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Abstract The 1H and 13C NMR spectroscopic properties of a series of furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-ones and -thiones were investigated. The influence of various electron donating as well as electron withdrawing substituents at C-5 or N-7 on 1H NMR chemical shifts as well as 13C chemical shifts at C8 were observed. The 5-chloromethyl group had a little influence on the chemical shift of H-7 proton and the 8-thione group causes deshielding of H-7 as well as H-5 protons in comparison with the C-8 carbonyl group.

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40

K., R. JYOTHIKUMARI, and N. RAJASEKHARAN K. "Synthesis of Furopyrimidines : Condensation of Alkyl/Aryl lsothiocyanates with 2-Amino-3-cyanofuran Derivatives." Journal of Indian Chemical Society Vol. 68, Dec 1991 (1991): 660–62. https://doi.org/10.5281/zenodo.5968806.

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Department of Chemistry, University of Kerala, Trivandrum-695 034 <em>Manuscript received 3 July 1990. revised 4 January 1991, accepted 4 December 1991</em> Condensation of a few 2-amino-3-cyano-4,5-disubstituted-furan with isotbiocyanates in the presence of a base has been found to result in the formation or 3-alkyl/aryl-4-imino-5. 6-disubstituted-furo[2, 3-<em>d</em>]pyrimidine-2-thiones (3a- n). These compounds on refluxing with aqueous dimetbylformamide was found to rearrange and form 4-arylaminofuro[1,3-<em>d</em>)pyridine-2-thiones.

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41

El-Sharkawy, Eman, and Yasser Selim. "Three new coumarin types from aerial parts of Ammi majus L. and their cytotoxic activity." Zeitschrift für Naturforschung C 73, no. 1-2 (2018): 1–7. http://dx.doi.org/10.1515/znc-2017-0068.

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AbstractThree new coumarin types were isolated from the aerial parts of the wild medicinal plantAmmi majus, which was collected from western Asia (Saudi Arabia), including pyrano coumarin, namely, 5-isobutylcoumarin-6-C-glucoside(1); furanocoumarin, namely, 6,7,9-Trimethoxy-3-(8′-methoxy-2′-oxo-2H-chromen-3-yl)-2H-furo[3,2-g]chromen-2(3H)-one(2); and pyrone coumarin, namely, 6-hydroxy-3-(2-hydroxypropyl)-7-methoxy-4 methyl coumarin(3). The structures were determined by spectroscopic methods, mainly 1D- and 2D-NMR. In vitro cytotoxicity was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphen

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42

Kh. Ahmed, Essam, and Mohamed A. Ameen. "Synthesis of thiopyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." Chinese Chemical Letters 21, no. 6 (2010): 669–73. http://dx.doi.org/10.1016/j.cclet.2009.12.010.

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43

Racha, Hanumandlu, Balakishan Vadla, Kavitha Peddolla, and Sailu Betala. "Synthesis and Anticancer Activity of Novel Hetero Ring Fused Pyridine Amide Derivatives." Asian Journal of Chemistry 31, no. 11 (2019): 2485–91. http://dx.doi.org/10.14233/ajchem.2019.22150.

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A series of novel hetero ring fused pyridine amide derivatives were prepared starting from ethyl furo[2,3-b]pyridine-2-carboxylate (3) on reaction with ammonia to afford furo[2,3-b]pyridine-2-carboxamide (4), compound 4 on reaction with trifluoroacetic acid to give compound 5, which on reaction with bromoethyl acetate followed by hydrazine hydrate to give compound 7. Compound 7 when reacted with different substituted aromatic aldehydes to give Schiff base compounds (8a-l). Similarly, compound 6a when reacted with diverse substituted aliphatic amines to give amide derivatives (9a-h). All the sy

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44

Krutošíková, Alžbeta, Miloslava Dandárová, and Juraj Alföldi. "Synthesis and Reactions of Furo[3,2-b]pyrrole Type Aldehydes." Collection of Czechoslovak Chemical Communications 58, no. 9 (1993): 2139–49. http://dx.doi.org/10.1135/cccc19932139.

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The synthesis of ethyl 2-formyl-4-benzylfuro[3,2-b]pyrrole-5-carboxylate (I) is described. A series of furo[3,2-b]pyrrole-2-carbaldehyde 2,6-dialkylphenylhydrazones (IIa - IIg) and dimethylhydrazones (IIIa - IIId) were prepared. By reaction of title compounds with hydroxylammonium chloride in acetic anhydride in the presence of pyridine corresponding cyano-substituted compounds (IVa - IVd) were obtained. Alkaline hydrolysis of IVa - IVd gave Va - Vb and the reaction with sodium azide and ammonium chloride in dimethylformamide led to VIa - VId. the structure of the compounds have been proved by

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45

Lichitsky, Boris V., Andrey N. Komogortsev, and Valeriya G. Melekhina. "2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid." Molbank 2021, no. 4 (2021): M1304. http://dx.doi.org/10.3390/m1304.

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For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the studied reaction proceeds in two steps including the initial interaction of starting materials in MeCN and the final formation of furylacetic acid moiety in acidic media. The structures of the obtained compound were established by 1H, 13C-NMR spectrosco

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46

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, form

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47

Elinson, Michail N., Varvara M. Kalashnikova, Yuliya E. Ryzhkova, and Oleg A. Rakitin. "3-Benzoyl-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone." Molbank 2025, no. 1 (2025): M1951. https://doi.org/10.3390/m1951.

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We describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone. The presented method is based on the cyclization of 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. It was shown that the presented reaction proceeds through the stage of bromination of the starting compound followed by O-nucleophilic attack. The structures of the obtained compound were established by 1H, 13C NMR and IR spectroscopy, and high-resolution ma

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48

Kráľová, Katarína, Renata Gašparová, and Martin Moncman. "Effect of 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxhydrazides on photosynthetic processes." Nova Biotechnologica et Chimica 7, no. 1 (2022): 115–21. http://dx.doi.org/10.36547/nbc.1367.

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A new series of carboxhydrazides 6-8 was synthesized under microwave irradiation by reaction of carboxhydrazide 1 with heterocyclic aldehydes 2-4 in the presence of p-toluenesulfonic acid in ethanol. N-Benzoylcarboxhydrazide 9 was prepared by reaction of 1 with benzoylchlorid 5 in THF at room temperature. The effects of 6-9 on inhibition of photosynthetic electron transport in spinach chloroplasts and chlorophyll content in the antialgal suspensions of Chlorella vulgaris were investigated.

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49

Elinson, Michail N., Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Artem N. Fakhrutdinov, and Mikhail P. Egorov. "Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase." Electrochem 2, no. 2 (2021): 295–310. http://dx.doi.org/10.3390/electrochem2020021.

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A continuously growing interest in convenient and ‘green’ reaction techniques encourages organic chemists to elaborate on new synthetic methodologies. Nowadays, organic electrochemistry is a new useful method with important synthetic and ecological advantages. The employment of an electrocatalytic methodology in cascade reactions is very promising because it provides the combination of the synthetic virtues of the cascade strategy with the ecological benefits and convenience of electrocatalytic procedures. In this research, a new type of the electrocatalytic cascade transformation was found: t

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50

Bozov, Petko I., Plamen N. Penchev, Tania D. Girova, and Velizar K. Gochev. "Diterpenoid Constituents of Teucrium scordium L. Subsp. scordioides (Shreb.) Maire Et Petitmengin." Natural Product Communications 15, no. 9 (2020): 1934578X2095952. http://dx.doi.org/10.1177/1934578x20959525.

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A new scordidesin А (1) and 2 known furo-clerodane diterpenoids, teucrin A (2) and 6-ketoteuscordin (3), were isolated by the phytochemical investigation of the acetone extract from the aerial parts of Teucrium scordium L. subsp. scordioides (Lamiaceae). The structure and stereochemistry of the compounds were established by high-resolution electrospray ionization mass spectrometry, infrared spectroscopy, and various 1H nuclear magnetic resonance (NMR) and 2-dimensional-NMR techniques. Additionally, we report 13C NMR spectral data of 3 that were not published before. Antimicrobial activity of t

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