New isatins was written by Buu-Hoi;Guettier, Haniel. And the article was included in Bulletin de la Societe Chimique de France in 1946.Synthetic Route of C10H9NO2 The following contents are mentioned in the article:
New halogenated or nitrated compounds are prepared from homologs of isatin. The starting materials were prepared by the Sandmeyer reaction (of. C.A. 13, 1840). Thus, 9-tert-butylindophenazine, m. 230°, results from heating o-C6H4(NH2)2 with the product of the Sandmeyer reaction (apparently 5-tert-butylisatin) in AcOH and crystallizing from alc. 5-Methylisatin (I) suspended in H2O containing a few grains of iodine and treated with a slow current of Cl several hours at a tepid temperature gives 5-methyl-7-chloroisatin, m. 180° (from alc.). I (10 g.) in 100 cc. cold H2SO4, treated with 6 g. KNO3 and poured into ice, gives about 1 g. 5-methyl-7-nitroisatin, m. 202-3° after reprecipitation from aqueous NaNO3 by HCl and recrystallization from boiling alc. Likewise, 2 g. 6-methylisatin in suspension, treated with 1 cc. Br 2 hrs., yields 5-bromo-6-methylisatin, m. about 200° (softens above 190°) after recrystallization from AcOH. 7-Methylisatin with Br gives 5-bromo-7-methylisatin, m. about 287°. Treating 5 g. 4,7-dimethylisatin (II) suspended in 500 cc. H2O with a slow stream of Cl gives about 3 g. 4,7-dimethyl-5-chloroisatin, m. 270-1° (from AcOH). Similarly, 10 g. II treated with Br 24 hrs. gives about 7 g. 4,7-dimethyl-5-bromoisatin, m. 298°. II with KNO3 in H2SO4 gives 4, 7-dimethyl-5-nitroisatin, m. 255°. A series of indophenazines was prepared by heating together in AcOH the isatin and o-C6H4(NH2)2 and recrystallizing from glacial AcOH or PhNO2. Empirical formulas and m.p. are: C15H10N3Br, m. 261°; C15H10N3Cl, m. 285°; C15H10O2N4, m. 319°; C16H13N3, m. 315° (sublimes above 290°); C15H11N3, m. 313° (sublimes above 260°); C15H10N3Br, m. 310-15°; C15H11N3, m. 313°; C15H10N3Br, m. 312°; C16H13N3, m. 309°; C15H12N3Cl, m. 319°; C10H12N3Br, m. 321°; C16H12O2N4, m. above 340°. A series of isatin 3-hydrazones are prepared by treating the isatin with excess N2H4.H2O in dilute alc. Empirical formulas are: C9H8ON3Br, m. 246° (decomposition); C9H8ON3Br, m. 256° (decomposition); C9H8ON3Br, decompose 220°; C9H3ON3Cl, decompose 198°. A series of isatin 3-phenylhydrazones results from adding PhNHNH2. dropwise to a saturated alc. solution of the isatin, boiling, cooling, and crystallizing from alc. Empirical formulas: C15H12ON3Br, decompose 287°; C15H12ON3Br, decompose 269-70°; C15H12ON3Br, 280°; C15H12ON3Cl, decompose 259-60°. N-Mercuric derivatives, prepared from all the above isatins by treating them in alc. with aqueous Hg(OAc)2 and crystallized from HOAc, m. above 350°. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Synthetic Route of C10H9NO2).
4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Synthetic Route of C10H9NO2
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