In connection with studies on the correlation of physiological action with chemical constitution the following dibenzofuran derivatives were prepared: 2-and 4-S-aminoethyldibenzofuran, 2and 3-fluorodibenzofuran, 4-dibenzofuryl-N-piperidinomethane, diethyl (3-dibenzofurylamino)ethylmalonate and diethyl (4-dibenzofurylamino)ethylmalonate. The synthesis of 3-and 4-(p-acetamidobenzenesulfonamido)dibenzofuran and of the corresponding amines was also cajrried out. The melting point of the 3-amide differed appreciably from previously recorded values. The interaction of 4-bromodibenzofuran with lithium dimethylamide and lithium diethylamide led to the rearrangement products: 3-dimethylaminodibenzofuran and 3-diethylaminodibenzofuran, respectively.
Metalation of Some Dibenzofuran Derivatives 951 these data are not quite in agreement with those given in the literature for 4,5-benzpyrene6 (m. p. 178-179°, picrate 229-230°), we believe that the structure is correct.peri-Naphthindone from -Naphthol.-a-Naphthol (72 g.) and acrolein (56 g.) were added simultaneously, within forty minutes, to anhydrous hydrofluoric acid (530 g.) at 15-20°. A sample of the condensation mass soon showed the bright green fluorescence in sulfuric acid, characteristic for ¿>m'-naphthmdone.A precipitate formed in the hydrofluoric acid, while the reaction mass was agitated overnight. The condensation mass was poured onto ice, and the suspension filtered and washed. A brown powder (105 g.) was obtained, which was soluble in sulfuric acid with a yellow color and a strong green fluorescence. Fifty grams of this product was extracted with 500 cc. of boiling dichlorobenzene. The solvent extract was steam distilled to remove the solvent, peri-Naphthindone crystallized from the water layer (4000 cc.) in light yellow crystals. Much tarry matter also was obtained. The pm'-naphthindone was identified by its melting point (151°), mixed melting point with a sample prepared according to German Patent 283,066, by its color and fluorescence in sulfuric acid. Similarly, perinaphthindone was obtained from /3-naphthol.Condensation of Acenaphthene with Acrolein.-Acrolein (28 g.) and acenaphthene (30.8 g.) were added to an-(5) J. W. Cook, C. L. Hewett and I. Hieger, J. Chevt. Soc., 395 (1933).hydrous hydrofluoric acid (370 g.) at 15-18°in ten minutes, and this solution was agitated for one hour at 10-15°. Acenaphthene showed no coloration in sulfuric acid, but the condensation product which formed as soon as acrolein was added dissolved in sulfuric acid with a brilliant green color. A finely divided precipitate formed while the charge was agitated at 15-20°for one hour. The reaction product isolated (51 g., light brown powder) after decomposition with ice had no melting point, dissolved in sulfuric acid with brilliant green color, and was only sparingly soluble in organic solvents with yellow color, and without appreciable fluorescence. A low melting product was isolated by extraction in a Soxhlet apparatus but could not be crystallized or identified. Summary "Peri" condensations which are not possible in sulfuric acid were performed in anhydrous hydrofluoric acid. "Peri" condensations obtained in sulfuric acid also could be performed in hydrofluoric acid. Perylene was obtained from phenanthrene and l,10-trimethylene-9-hydroxyphenanthrene, 4,5-benzpyrene from 9,10-dihydroanthracene, and pen-naphthindone from a-and /3-naphthol. Wilmington, Del.
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