Reaction of certain diazosulfonates derived from 2-naphthol-1-sulfonic acid. XXVI. Phthalazine and isoindolinone compounds derived from aniline was written by Peters, A. T.;Rowe, F. M.;Brodrick, C. I.. And the article was included in Journal of the Chemical Society in 1948.Name: 2-Phenylisoindolin-1-one This article mentions the following:
PhN2Cl (from 100 g. PhNH2), added to an ice-cold solution of 400 g. 50% 2,1-HOC10H6SO3Na in 1200 cc. H2O, the 2-naphthol-1-benzenediazosulfonate (salted out with NaCl) converted by 100 g. Na2CO3 in 400 cc. H2O at 0闂?to Na 1-benzeneazo-2-naphthoquinone-1-sulfonate (I), the mixture (after 15 min.) treated at 5闂?with 100 g. NaOH in 300 cc. H2O, and then (after 15 min.) acidified with HCl at a temperature below 10闂? gives a tar which, on solution in NH4OH and addition to boiling dilute HCl, gives 63% 1-hydroxy-3-phenyl-3,4-dihydro-4-phthalazineacetic acid (II), m. 264闂?(decomposition); Et ester, m. 91-2闂? boiling with Ac2O 4 hrs. gives the O-acetate, m. 183闂? boiling with Ac2O and a little C5H5N 50 hrs. gives also 4% of the internal anhydride of II, C16H12O2N2, m. above 320闂? 1-Keto-3-phenyl-2-methyltetrahydro-4-phthalazineacetic acid, m. 184-6闂? II (7 g.) and 15 cc. fuming HCl, heated 1 hr. at 180闂?and the product heated 10 min. with 15% Na2CO3, give 97% 3-phenyl-1-phthalazone (III), m. 208闂? turns green on standing (HCl salt, m. 162-4闂? picrate, yellow, m. 226闂?; Me2SO4 at 80闂?gives a resin which, boiled 5 min. with EtOH, gives the compound C17H18O2N2, m. 86-7闂? heated 4 hrs. at 140闂? this yields a compound C16H12ON2, yellow, m. 234闂?(decomposition). III (2 g.), 140 cc. HCl, 80 cc. H2O, 40 cc. EtOH, and 200 g. Zn-Hg, heated 4 hrs. at 70-80闂? give 85% 2-phenylphthalimidine. II (10 g.) in 70 cc. AcOH at 20闂? treated (2 hrs.) with 4 g. CrO3 in 20 cc. AcOH and 10 cc. H2O and the mixture kept overnight, gives 35.9% 3-phenyl-4-methyl-1-phthalazone (IV), m. 235闂?(picrate, yellow, m. 197闂?; 2 g. IV and 4 g. Na2S2O4 in dilute aqueous NaOH, boiled 10 min., give 44.7% 1-keto-3-phenyl-4-methyltetrahydrophthalazine, m. 171闂? IV (3 g.), 70 cc. HCl, 50 cc. H2O, and 90 g. Zn-Hg, boiled 4 hrs., give 2-phenyl-3-methylphthalimidine, m. 80闂? II (10 g.), added (30 min.) to 70 cc. HNO3 at below 10闂?and the mixture poured onto ice, gives 73.6% of the 4′-NO2 derivative of IV. II, refluxed 40 min. with aqueous H2SO4 (b. 140闂? or with equal volumes of H2SO4 and AcOH, gives 3-phenyl-1-phthalazone-x-sulfonic acid, prismatic needles with no m.p. I (from 50 g. PhNH2) in aqueous Na2CO3 at 0闂? added to 50 g. NaOH in 180 cc. H2O at 0闂? the mixture acidified after 5 min., the Na salt hydrolyzed, the acid solution evaporated to dryness, and the product extracted with and fractionated from AcOEt, gives 6.6 g. I; the more soluble fraction, boiled 5 min. with Ac2O, gives 1.3 g. 2,5-diketo-3-phenylisoindolinopyrazolidocoline, m. 220-1闂? the 2,4-dinitrophenyl derivative m. 238-9闂?(cf. C.A. 42, 4568d). In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 2-Phenylisoindolin-1-one
Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles