Chemical studies in relation to the biosynthesis of some natural benzofurans and related compounds. I was written by Nurunnabi, B. I.. And the article was included in Pakistan Journal of Scientific and Industrial Research in 1960.Recommanded Product: Methyl benzofuran-2-carboxylate This article mentions the following:
The formation of benzofurans by loss of an iso-Pr group from an isopropylfuran, formed by cyclization of an isopentenyl sidechain, was investigated. 6-Methoxycoumaran-3-one (I) (0.5 g.) in absolute EtOH was treated with NaBH4 to give 6-methoxybenzofuran (II), b1.5-2.0 67°, n18D 1.5664 (picrate m. 64°; trinitrobenzoate m. 56°), and 3-(6-methoxy-2-benzofuranyl)-6-methoxybenzofuran (III), m. 144-5°. 6-Methoxy-2-isopropylidenecoumaran-3-one (IV) (1.5 g.) treated with NaBH4 gave 2,2-bis(6-methoxycoumaran-3-onyl)propane (V), m. 203-4°, and II, b0.8 80°. IV (100 mg.) in 10 ml. absolute EtOH was refluxed 40 min. under N with 50 mg. Na hyposulfite in 0.5 ml. 10% NaOH to give Me2CO and V. IV (50 mg.) and 50 mg. I in absolute EtOH with 2 drops 10% NaOH gave V. o-Allylphenol (67 g.) in 79 g. C5H5N treated with excess BzCl gave the ester (VI), b1.5 162°. V (11.9 g.) in 42.3 ml. HCO2H was treated with 5.9 g. 30% H2O2 at 40°. After 2 hrs. the mixture was worked up to give an oily residue, which was hydrolyzed by refluxing 2 hrs. with aqueous methanolic NaOH to give 1-(o-hydroxyphenyl)propane-2,3-diol (VII), b1.2 175°. Oxidation of VII with HIO4 or Pb(OAc)4 gave polymers. To 10 g. anhydrous Na2SO4, 20 ml. absolute EtOH and 2 ml. 1% OsO4-Et2O was added alternately 7.3N H2O2-Et2O and 2.5M VI-Et2O, after 1 day the HCHO removed with CO2 gas, and the mixture worked up to give 1-(o-benzoyloxyphenyl)propane-2,3-diol (VIII), m. 82°. VIII (2 g.) in 100 ml. 70% EtOH was treated with 5.7 g. K periodate in 200 ml. N H2SO4 to give, after treatment of the product with semicarbazide-HCl, o-benzoyloxyphenylacetaldehyde semicarbazone, m. 184°. Attempted removal of the benzoyloxy group gave only resins. Benzyloxyallylbenzene (IX) (11.9 g.) was added to 7.6 g. perbenzoic acid in 140 ml. CHCl3 to give after 4 days at 0° IX epoxide, b1.5 173°, which was treated in EtOH with NaOH 5 days to give 60% 2-(hydroxymethyl)coumaran (X), b1.0 108°; 3,5-dinitrobenzoate m. 114.5°. The benzoate of 2-hydroxy-4-methoxyallylbenzene was similarly prepared, b1.1 173°, and converted to the epoxide (XI), b0.75 196°. Alk. alc. hydrolysis of XI gave 2-hydroxymethyl-6-methoxycoumaran, b1.5 138°; 3,5-dinitrobenzoate m. 140°. The epoxide (XII) of suberosin was prepared, m. 120-1°. XII (2 g.) and 1 g. red P were added to 150 ml. HBr (d. 1.5) and the mixture refluxed 1 hr. to give anhydronodakenetin (XIII), m. 136-7°. Coumarilic acid with MeOH and HCl gave Me coumarilate, m. 54-5°, reduced with LiAlH4 in Et2O to X. X was further reduced with Na in EtOH to 2-methylcoumarone, b2.0 52°. Epoxidation of isopentenyl or allyl sidechains appeared to be an intermediate step in the biogenesis of benzofurans. Furans did not appear to arise from the oxidation of glycolic C5 or C3 sidechains. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Recommanded Product: Methyl benzofuran-2-carboxylate).
Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Recommanded Product: Methyl benzofuran-2-carboxylate
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem