Reactivity of the carbonyl group and of dehydrogenation activity of isatin compounds. II was written by Giovannini, E.;Portmann, P.;Johl, A.;Schnyder, K.;Knecht, B.;Zen-Ruffinen, H. P.. And the article was included in Helvetica Chimica Acta in 1957.Name: 4,7-Dimethylindoline-2,3-dione The following contents are mentioned in the article:
The dehydrogenation activity of many mono- and disubstituted derivatives of isatin (I) expressed as time of decolorization of a methylene blue (II) solution according to Langenbeck (C.A. 21, 2126) have been measured and tabulated as relative activities to that of I (100), using 10-4 or 2 × 10-5 mole compound in 5 cc. pyridine and 2 cc. standard aqueous solution [2 g. DL-MeCH(NH2)CO2H (III), 0.3737 g. II, and 10 cc. AcOH made up to 100 cc.] (isatin substituent, m.p., decoloration time (min.) with 10-4 and 2 × 10-5 mole, relative dehydrogenation activity given): H, 200°, 10, 50, 100; 4-Me, 190-2°, > 1320, -, < 0.75; 5-Me, 186-7°, 11, 50, 95; 6-Me, 190-1°, 19, 72, 61; 7-Me, 266°, -, 31, 161; 4-Cl, 259-60°, 113, -, 8.8; 5-Cl, 251-3°, 7, 42, 131; 6-Cl, 263°, 8, -, -; 7-Cl, 188-90°, 6, 33, 159; 4-NO2, 245°, > 900, -, < 1.1; 5-NO2, 253°, 12, 68, 88; 6-NO2, 288-90°, 7, 48, 123; 7-NO2, 237°, -, 42, 119; 4-NH2, 254-5°, > 900, -, < 1.1; 5-NH2, above 330°, 12, 65, 80; 7-NH2, above 330°, -, 52, 96; 4-HO, 260° (decomposition), 73, -, 13.7; 5-HO, above 290° (decomposition), 9, -, 111; 6-HO, above 325° (decomposition), 127, -, 7.8; 5-MeO, 201-2°, 9, 43, 114; 6-MeO, 229-30°, 69, -, 14.4; 7-MeO, 240-2°, 7, 33, 147; 4-CO2H, 285°, -, 1.5, 3300; 5-CO2H, 295°, 7, 32, 150; 6-CO2H, 328-30°, -, 28, 178; 7-CO2H, 277°, -, 32, 156; 4-SO3H, 183° (decomposition), 4, -, 250; 5-SO3H, 145-7°, 19, -, 52; 6-SO3H, above 290° (decomposition), 15, -, 67; 7-SO3H, m. above 350° (decomposition), 19, -, 52. Substituents in the 4-position have a great influence, in one sense or another, on the dehydrogenation activity of I and probably on the activity of the 3-CO group. The effect of the 4-CO2H group is not due to its acid character as shown by the relative dehydrogenation activities of the 4-HO and 4-SO3H substituted compounds The effect of double substitution was examined: 4,6-Me2, 241-3°, > 900, -, < 1.1; 4,7-Me2, -, > 900, -, < 1.1; 5,6-Me2, 212-13°, 20, -, 50; 4,7-Me(CO2H), 258-60°, > 900, -, < 1.1; 7,4-Me(CO2H), 295°, -, 1.5, 3300; 4,7-(CO2H)2, 303-5°, -, 3.5, 1430; 4,7-Cl2, 246°, 89, -, 11.2; 5,6-(HO)2, 290° (decomposition), 230, -, 4.3; 5,6-Cl(HO), 284-6°, 236, -, 4.2; 5.6-(MeO)2, 252°, 75, -, 13.3; 5,6-CH2O2, 284°, 60, -, 16.6. The inactivation caused by the 4-Me group persists. The effect of 2 activating groups is not additive but groups with contrary effects may give an intermediate value. Since the inactivation caused by some 4-substituents might be attributable to steric effects, the dehydrogenation activities with H2NCH2CO2H (IV) have been compared with those with III [isatin substituent, times (min.) of decolorization with III and IV, ratios of activity (III/IV) given]: H, 10, 4, 2.5; 4-Me, > 1310, 108, > 13; 5-Me, 11, 4, 2.7; 6-Me, 18, 7, 2.5; 4,6-Me2, > 900, 205, > 4.4; 4,7-Me2, > 900, 131, > 6.9; 4-Cl, 113, 12, 9.4; 4-NO2, > 900, 280, > 3.2; 4-CO2H, 1.5, 0.75, 2. The activity of 4-methylisatin is less than that of the other isomers against IV and no explanation is offered for the activity of 4-carboxyisatin. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Name: 4,7-Dimethylindoline-2,3-dione).
4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Name: 4,7-Dimethylindoline-2,3-dione
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles