Synthesis of Geminally Activated 4-(Furan-2-yl)- and 4-(Thiophen-2-yl)-1-nitrobuta-1,3-dienes

The condensation of 3-(furan-2-yl)- and 3-(thiophen-2-yl)prop-2-enals with nitro-substituted CH acids, namely ethyl nitroacetate, nitroacetone, nitroacetophenone, and nitroacetonitrile, afforded a series of geminally activated nitro dienes, 4-(furan-2-yl)- and 4-(thiophen-2-yl)-1-nitrobuta-1,3-dienes. The product structure was confirmed by NMR and IR spectroscopy.

     

Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole

Reaction of 1,2-diamino-4-nitrobenzene with furan-2-carbaldehyde in the presence of copper sulfate afforded 2-(furan-2-yl)-5(6)-nitro-1H-benzimidazole. Its N-methylation provided 1-methyl-5(6)-nitro isomers. After reduction of isomers with tin in conc. HCl a pure 3-methyl-2-(furan-2-yl)benzimidazol-5-amine was obtained. The condensation of this amine with acetic anhydride led to the formation of N-[3-methyl-2-(furan-2-yl)benzimidazol-5-yl]acetamide whose treatment with excess P₂S₅ in anhydrous pyridine resulted in the corresponding thioamide. The latter was oxidized with K₃[Fe(CN)₆] in alkaline environment to obtain 2,8-dimethyl-7-(furan-2-yl)-8H-imidazo[4,5-g][1,3]benzothiazole. Its reactions of electrophilic substitution were studied: nitration, bromination, sulfonation, formylation, acylation. The substituent is introduced exclusively in the position 5 of the furan ring.     

Synthesis,Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole, a novel compound, was synthesized by the annulation of 5-hydroxyethylcarbamoyl-4-methyl-2-(4- methylphenyl)-1,3-thiazole with P_2S_5. 5-Hydroxyethylcarbamoyl-4-methyl-2-(4-methylphenyl)-1,3-thiazole was prepared from the starting material of p-tolunitrile. The newly synthesized compounds were characterized by elemental analysis, IR, NMR(~1H, ~(13)C) and MS spectra. Hence, the crystal of the title compound was obtained, and its structure was determined by X-ray diffraction analysis. The crystal belongs to the triclinic system, space group P1 with a = 7.354(4), b = 8.383(4), c = 11.543(6) ?, α = 76.688(6), β = 72.299(6), γ = 88.157(6)°, V = 659.2(6) ?~3, Z = 2, M_r = 274.39, D_c = 1.382 g/cm~3, μ = 0.386 mm~(-1), F(000) = 288, R = 0.0586 and w R = 0.1808 for 2984 unique reflections with 2213 observed ones(I 2σ(I)). The title compound was also screened for its antibacterial activities against Bacillus subtilis and Escherichia coli. The result indicates that the target compound presents potential antimicrobial activities, and that the minimum inhibitory concentration(MIC) values of the title compound against the two tested strains are both 62.5 μg/mL.     

Synthesis and Some Properties of 2-(Furan-2-yl)[1,3]thiazolo[4,5-b]pyridine

Russian Journal of Organic Chemistry - The acylation of pyridin-2-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(pyridin-2-yl)furan-2-carboxamide, and treatment of the latter with...     

Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles

Russian Journal of General Chemistry - Reaction of 2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide with dimethylamine gave 5-(dimethylamino)-2-[(dimethylamino)methyl]-1,3-oxazole-4-carbonitrile,...     

Synthesis of 2-(1,3-Diselenan-2-yl)thiophene from 1,3-Propanediselenol and 2-Thiophenecarbaldehyde

Russian Journal of Organic Chemistry -     

Synthesis and isomerization reaction of 2-(benzoxazol-2-yl)-1,3-tropolones

An acid-catalyzed reaction of 2-methylbenzoxazole with 3,4,5,6-tetrachloro-1,2-benzoquinone leads to 2-(benzoxazol-2-yl)-5,6,7-trichloro-1,3-tropolone and 2-(benzoxazol-2-yl)-4,5,6,7-tetrachloro-1,3-tropolone. 1,3-Tropolones upon reflux in ethyl alcohol undergo the rearrangement resulted in the seven-membered ring contraction to form ethyl 2-(benzoxazol-2-yl)-5,6-dichloro-3-hydroxybenzoate and ethyl 2-(benzoxazol-2-yl)-4,5,6-trichloro-3-hydroxybenzoate. The molecular structure of the latter was established by X-ray diffraction analysis.     

Synthesis and reactivity of 2-(porphyrin-2-yl)-1,3-dicarbonyl compounds

A simple and efficient procedure for the synthesis of porphyrins bearing 1,3-dicarbonyl moieties at the β-position is described. The new compounds were further functionalized and new derivatives containing an heterocyclic ring, an ethyl acetate residue or a 2-oxopropyl group at the β-position have been obtained.     

Synthesis of 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds

Reaction of dibenzosuberen-5-ol with 1,3-dicarbonyl compounds catalyzed with scandium(III), copper(II), or indium(III) triflate (5 mol %) afforded 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds in 63–86% yield.     

5-(呋喃-2-基)-3-苯基异噁唑的合成及其对硫酸盐还原菌的抑制活性

苯乙酮和呋喃甲醛在氢氧化钠作用下制得3-(呋喃基-2)-1-苯基-丙烯酮(1);1与羟氨经串联反应(缩合、加成和氧化芳构化)合成了5-(呋喃-2)-3-苯基异噁唑(3),总收率41.2%,其结构经NMR和MS表征。抑菌活性测试结果表明,3用作油田杀菌剂对硫酸盐还原菌有一定的抑制作用。     

Synthesis of 1,3-dialkyl-5-(hetaryl-1-yl)-1,3-dihydrobenzimidazol-2-ones

Reactions of 5-amino-1,3-dialkyl-1,3-dihydrobenzimidazol-2-ones with 2,5-dimethoxytetrahydrofuran and 2,6-dimethyl-γ-pyranone led to the formation of 1,3-dialkyl-1,3-dihydro-5-(pyrrol-1-andл)benzimidazol-2-ones and 1-(1,3-dialkyl-2-oxo-1,3-dihydrobenzimidazol-5-yl)-2,6-dimethylpyridin-4-ones.     

Synthesis and molecular structure of 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazines

Reactions of some 2-hydrazinopyrimidine hydrochlorides with potassium thiocyanate gave 1-(pyrimidin-2-yl)thiosemicarbazides which underwent Hantzsch condensation with aryl chloromethyl ketones to produce 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazine hydrochlorides. The protonation was accompanied by mutually dependent tautomeric rearrangements of heterocyclic fragments.     

Synthesis and Reactivity of 2-(Thiophen-2-yl)[1,3]thiazolo[4,5-f]quinoline

Russian Journal of Organic Chemistry - The condensation of quinolin-5-amine with thiophene-2-carbonyl chloride in propan-2-ol gave N-(quinolin-5-yl)thiophene-2-carboxamide. Treatment of the latter...     

Synthesis of new 1,3-thiazole derivatives from 2(5)-hydroxyalkyl-1,3-thiazole-5(2)-carbaldehydes

Reactions of substituted 2-hydroxyalkyl-1,3-thiazole-5-carbaldehydes and 5-hydroxyalkyl-1,3-thiazole-2-carbaldehydes with phenylhydrazine, isoniazid, N-substituted rhodanines were performed as well as Biginelli reaction with acetoacetic ester and urea. As a result, new 1,3-thiazole derivatives were obtained. They are of interest as potential bioactive substances.     

Synthesis and Crystal Structure of Tert-butyl 4-[(E)-4-(1,3 -Dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-butenyl] Benzoate

1 INTRODUCTION Phthalimide and its derivatives are synthetic mate- rials, which are widely used as important chemical intermediates of biosensors[1] and many drugs such as Citalopran[2], luminal[3], Beta-Lactam[4] and the No. three generation quinolones[5], and they have been identified as active groups of some drugs and chemical luminescence reagents[6, 7]. Tert-butyl 4- [(E)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1- butenyl] benzoate is an intermediate of a new type of insulin sen…     

Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives,and Study of Their Antimicrobial Activity

Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus.