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A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatization, and acetylation reactions. The measurement of the electron transport chain in spinach chloroplasts showed that several derivatives are capable of interfering with the photosynthetic apparatus. Few of them were found to inhibit the basal rate, but a significant inhibition was brought about only at concentrations exceeding 50 muM. Some other analogues acted as uncouplers or energy transfer inhibitors, with a remarkably higher effectiveness. Isobenzofuranone addition to the culture medium inhibited the growth of the cyanobacterium Synechococcus elongatus, with patterns consistent with the effects measured in vitro upon isolated chloroplasts. The most active derivatives, being able to completely suppress algal growth at 20 muM, may represent structures to be exploited for the design of new active ingredients for weed control.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1503O – PubChem

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Certain 4- and 5-oxoacids may exist in their cyclic lactol (or pseudoacid) forms. These commonly occur in compounds with proximate carboxylic acid and carbonyl (aldehyde or ketone) functions for the formation of five- or six-membered rings. Examples include trans-2,3-disubstituted aliphatic, (Z)-2,3-olefinic and o-disubstituted aromatic acids. Crystal structures of compounds in these categories are reported: trans-4-methyl-3-oxo-6-hydroxytetrahydropyran-3-carboxylic acid (6), monoclinic, C2/c, a = 25.412 (5), b = 6.291 (1), c = 10.757 (2) A, beta = 104.84 (3); penicillic acid (7), 4-methoxy-5-hydroxy-5-(2?-propenyl)dihydrofuran-2-one, tetragonal, P42/n, a = b = 15.83 (2), c = 7.016 (11) A; mucochloric acid (8), (Z)-3,4-dichloro-5-hydroxydihydrofuran-2-one, triclinic, P1, a = 6.227 (5), b = 8.085 (5), c = 12.369 (9) A, alpha = 99.50 (5), beta = 102.38 (6), gamma = 90.29 (6); 2-methanoylbenzoic acid (9), 3-hydroxy-1-(3H)-isobenzofuranone, monoclinic, P21, a = 4.006 (1), b = 11.489 (2), c = 7.347 (1) A, beta = 97.50 (3); 2-ethanoylbenzoic acid (10), 3-hydroxy-3-methyl-1-(3H)-isobenzofuranone, orthorhombic, P212121, a = 5.199 (6), b = 9.651 (14), c = 15.950 (17) A; 2-(2?-oxoethyl)benzoic acid (11), 3-hydroxy-3,4-dihydroisobenzopyran-l-one, monoclinic, P21/n, a = 4.651 (3), b = 11.886 (7), c = 14.312 (11) A, beta = 90.86 (6). These compounds also exist in the cyclic forms in chloroform solution. A trimeric cyclic trioxane structure, analogous to paracetaldehyde, is confirmed as the solid form of 5-oxopentanoic acid (1), triclinic, P1, a = 5.640 (4), b = 8.571 (8), c = 18.962 (13) A, alpha = 78.68 (6), beta = 84.34 (5), gamma = 80.38 (6). In solution (NMR), mixtures of the open aldoacid, trimeric acid and cyclic pseudoacid exist. In both furanoid and pyranoid pseudoacids, endocyclic lactol C-O bond lengths are lengthened (1.46-1.48 A), while the exocyclic C-O(H) bonds are shortened (1.38 A). Pseudoacids commonly form hydrogen-bonded chains linking the lactol hydroxy and carbonyl groups, but 3-hydroxy-3,4-dihydroisobenzopyran-1-one forms distinctive hydrogen-bonded dimers.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1508O – PubChem

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The directed ortho-lithiation-alkylation of several tertiary beta-amino benzamides was studied.The ortho-substituted beta-amino benzamides were hydrolyzed directly with 6 N hydrochloric acid, or by a three-step, one-pot reaction involving methylation, elimination, and treatment with aqueous acid. o-Toluic acid, 2-n-butylbenzoic acid, 2-methoxy-6-methylbenzoic aicd, and 4-methoxy-2-methylbenzoic acid were prepared by using this ortho-metalation-hydrolysis methodology.Ortho-lithiation and reaction with benzaldehyde or dimethylformamide followed by hydrolysis with aqueous acid gave lactones in good yield.Methanolysis of N-(4-methoxy-2-methyl benzoyl)-N’-methylpiperizine with sulfuric acid/methanol gave methyl 4-methoxy-2-methylbenzoate in 71percent yield.The conversion of tertiary benzamides into ketones and aldehydes was examined.Treatment of certain tertiary benzamides with alkyllithium reagents gave ketones, while reaction with a modified aluminum hydride reagent gave aldehydes

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Benzofuran – Wikipedia,
Benzofuran | C8H1451O – PubChem

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New aminophthalides were synthesized from o-formylbenzoic acid and substituted 2-aminothiophenes. Two of these compounds underwent recyclization in boiling Ac2O to give the previously unknown 3-acetoxy-2-(3-cyano-4, 5-dimethylthiophen-2-yl)-1,3-dihydroisoindol-1-one and 3-acetoxy-2-(3-cyano-4,5- tetramethylenethiophen-2-yl)-1,3-dihydroisoindol-1-one. The possible reaction mechanism and factors preventing the recyclization, in particular, the formation of intramolecular hydrogen bonds in the starting phthalides, were discussed. Some reactions of the resulting compounds with C-nucleophiles in trifluoroacetic acid were investigated. Two derivatives containing 4-hydroxy-3,5-di-tert- butylphenyl substituents were studied by X-ray diffraction.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1507O – PubChem

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The generality of the [CpCoL2]-mediated [2+2+2] cycloaddition of , alpha omega-diynes to (cyclo)alkenes has been extended to include linear oligocycles as models for the one-step, A + D? ABCD construction of optically pure, novel 6,10-dihydroanthracyclinones. Georg Thieme Verlag Stuttgart – New York.

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Benzofuran – Wikipedia,
Benzofuran | C8H1437O – PubChem

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Subcritical water (<374C and <221 bar) has unique characteristics such as dramatically decreased dielectric constant, surface tension, and viscosity with increasing temperature, allowing for dissolution and reaction of organics in high-temperature water to occur. Additionally, the dissociation constant of water at temperatures of 200-300C is three orders of magnitude greater than that of ambient water, which may also contribute to the reactivity of subcritical water with certain organic compounds. In this study, the degradation and oxidation of phenanthrene in subcritical water were investigated. Both deionized water and water with 3% hydrogen peroxide were used in the degradation and oxidation studies. The effect of temperature on degradation efficiency has been determined with a temperature range of 100-350C. When the temperature was increased from 150 to 350C, the amount of phenanthrene degraded varied from 6 to 243 mug in each milliliter of deionized water. However, these quantities were increased to 195 mug at 150C and 3680 mug at 350C in each milliliter of water with 3% hydrogen peroxide. Several degradation products including phenol, benzoic acid, and ketones were identified by using gas chromatography/mass spectrometry (GC/MS). Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Synthetic Route of 16859-59-9. In my other articles, you can also check out more blogs about 16859-59-9

Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1513O – PubChem

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A new synthetic route for the conversion of substituted 3-hydroxyphthalides into the corresponding isoquinolin-1(2H)-one was established. This method can be applied to the preparation of isoquinolin-1(2H)-ones with electron-withdrawing groups that are relatively difficult to synthesize by conventional procedures.

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Benzofuran – Wikipedia,
Benzofuran | C8H1501O – PubChem

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This work reports the design and synthesis of novel alkylamides, characterized by a dibenzo[a,d] cycloheptene nucleus, as melatonin (MLT) receptor ligands. The tricyclic scaffold was chosen on the basis of previous quantitative structure-activity studies on MT1 and MT2 antagonists, relating selective MT2 antagonism to the presence of an aromatic substituent out of the plane of the MLT indole ring. Some dibenzo seven-membered structures were thus selected because of the noncoplanar arrangement of their benzene rings, and an alkylamide chain was introduced to fit the requirements for MLT receptor binding, namely, dibenzocycloheptenes with an acylaminoalkyl side chain at position 10 and dibenzoazepines with this side chain originating from the nitrogen atom bridging the two phenyl rings. Binding affinity at human cloned MT1 and MT2 receptors was measured by 2[125I] iodomelatonin displacement assay and intrinsic activity by the GTPgammaS test. The majority of the compounds were characterized by higher affinity at the MT2 than at the MT 1 receptor and by very low intrinsic activity values, thus confirming the importance of the noncoplanar arrangement of the two aromatic rings for selective MT2 antagonism. Dibenzocycloheptenes generally displayed higher MT1 and MT2 affinity than dibenzoazepines. N-(8-Methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ylmethyl)propionamide (4c) and -butyramide (4d) were the most selective MT2 receptor antagonists of the series, with MT2 receptor affinity comparable to that of melatonin and as such among the highest reported in the literature for MLT receptor antagonists. The acetamide derivative 4b produced a noticeable reduction of GTPgammaS binding at MT2 receptor, thus being among the few inverse agonists described.

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Benzofuran – Wikipedia,
Benzofuran | C8H1475O – PubChem

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Anionic [4+2] annulation of lithiated furoindolones with dimethyl maleate followed by selective demethoxycarbonylation provides an efficient synthetic route to 3-methoxycarbonylcarbazoles. The route has led to the straightforward synthesis of two natural products, namely clausine E, mukonine, and their 4-prenyl analogues. A new route to cyclohepta[d,e,f]carbazole was also uncovered during the investigations.

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Benzofuran – Wikipedia,
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A palladium(II)-catalyzed cascade approach was established for the synthesis of indeno[1,2-c]isochromen-5(11H)-ones starting from 2-alkynyl tert-butyl benzoates bearing a pendant alpha,beta-unsaturated carbonyl moiety in high yields (up to 99%) under mild conditions. This strategy offered high atom and step economy by delivering isobutene as the only side product, and by generating two new bonds and two rings in a single synthetic operation. The mechanism of the cascade process was visualized comprising sequential intramolecular oxypalladation (6-endo-dig), intramolecular olefin insertion, and protonation steps. (Figure presented.).

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1464O – PubChem