Indol-3-ones

Fig. 26 Solid-phase synthesis of indol-2-ones by microwave-assisted radical cyclization. Reagents and conditions a NaH, DMF b BusSnH, AIBN, DMF, MW 170 °C, 45 min, sealed vessel c 10% TFA in CH2CI2. R = H, F, Me, OCF3 R = Phe, 3-OMe - Phe, 4-Me - Phe, 3,4-0CH20-Ph, (CH2)4, diMe R" = H, Me R " = H, Me...

RN 115-33-3 MF C24H,yN05 MW 401.42 EINECS 204-083-6 CN 3,3-bis[4-(acetyloxy)phenyl]-l,3-dihydro-2ff-indol-2-one... 

CN 5-[2-[4-(l,2-Benzisothiazol-3-yl)-l-piperazinyl]ethyl]-6-chloro-l,3-dihydro-2//-indol-2-one hydrochloride hydrate... 

Scheme 7.7 Solid-phase synthesis of indol-2-ones through radical cyclization.

TV-Acetyl indolin-3-one 123 was converted to 3-cyanomethyl-3-(l,l-dimethylallyl) indol-2-one, 127, by a successive isomerization-Claisen rearrangement sequence (equation 63)91.7V-Acetylindolin-3-one 123 was converted in two steps to a mixture of E- and Z-isomers of 124. Isomerization of both isomers of 124 to 125 was accomplished with DBU. Claisen rearrangement of 125 afforded a 13% yield of 126, which was subsequently deprotected to give 3-cyanomethyl-3-(l,l-dimethylallyl)indol-2-one, 127, in 47% yield. 

Biological In 9% anaerobic municipal sludge, indole degraded to l,3-dihydro-2/7-indol-2-one (oxindole), which degraded to methane and carbon dioxide (Berry et al, 1987). Heukelekian and Rand (1955) reported a 5-d BOD value of 1.70 g/g which is 65.4% of the ThOD value of 2.48 g/g. 

Kalinski C, Umkehrer M, Ross G, Kolb J, Burdack C, Hiller W (2006) Highly substituted indol-2-ones, quinoxalin-2-ones and benzodiazepin-2, 5-diones via a new Ugi(4CR)-Pd assisted A-aryl amidation strategy. Tetrahedron Lett 47 3423-3426... 

Umkehrer M, Kalinski C, Kolb E, Burdack C (2006) A new and versatile one-pot synthesis of indol-2-ones by a novel Ugi-four-component-Heck reaction. Tetrahedron Lett 47 2391-2393... 

Synthesis of high Tg co-polycarbonates containing 3,3-bis(4-hydroxyphenyl)-l-phenyl-lH- indol-2-one and bisphenol A biphenols, which adhere to aluminum. 

The bisphenol 3,3-bis(4-hydroxyphenyl)- l-phenyl- l II-indol-2-one was prepared in a single step from /V-phenylisatin and molten phenol and not through the use of a phenolphthalein derivative. Although phenylisatin could have also been prepared through a modified isonitrosoacetanilide isatin process, it was formed in a one-pot process by reacting oxalic acid dichloride and aluminum chloride with diphenylamine. 

TABLE 1. Physical Properties of Polycarbonate Prepared Using Bisphenol A, 3,3-bis(4-hydroxy-phenyl)-l-phenyl-lH-indol-2-one, and Phosgene Dissolved in C Cb/Chlorobenzene at Ambient Temperature... 

The heterocyclization of peri-aminonaphthoyl compounds allows the preparation of three main types of benzo[crf]indole series, namely, bases 113, benzo[crf]indolium salts 114, and benzo[crf)indole-2-ones 115. Because closure to the nitrogen heterocycle is so facile, peri-amino-substituted naphthaldehydes and naphthyl ketones, even under conditions of their formation, are converted into benzo[crf]indoles 113. Those unsubstituted in position 2, as well as 2-alkyl-substituted benzo[cd]indoles 113 (R = H, Aik), have not been isolated because of their easy oxidation by air. 

Naphthostyryl 115 (R = R = H) and its numerous N-and naphthalene-substituted derivatives are obtained by acid-catalyzed heterocyclization of peri-aminonaphthoic acids 139. One should notice it is not necessary to isolate these acids since, as a rule, conditions of their formation are suitable for heteroring closure. Syntheses of benzo[crf]indole-2-ones 115 are carried out in a number of ways ... 

Fuchs JR, Funk RL (2005) Indol-2-one Intermediates Mechanistic Evidence and Synthetic Utility. Total Syntheses of ( )-Fhistramines A and C. Org Lett 7 677... 

Chemical Name 2H-Indol-2-one, l,3-dihydro-4-(2-(dipropylamino)ethyl)-, monohydrochloride... 

A clean and dry 20-gallon reactor was charged with 17.4 gallons of deionized water and 4.44 L of concentrated hydrochloric acid, to give a 0.77 M solution. To the solution was added 4.44 kg of the anhydrous 5-(2-(4-(l,2-benzisothiazol-yl)-l-piperazinyl)-ethyl)-6-chloro-l,3-dihydro-2H-indol-2-one free base. The slurry was warmed to 65°C and held for 18 hours. The slurry was cooled to room temperature. The product was filtered and washed with 2x5-gallon portions of deionized water, and then air dried at 50°C for 30 hours. The dried product contained 4.4% water and the x-ray diffraction method confirmed that the desired product was obtained. 

Spencer J, Mendham AP, Kotha AK, Richardson SCW, Hillard EA, Jaouen G, Male L, Hursthouse MB (2009) Structural and biological investigation of ferrocene-substituted 3-methylidene-l, 3-dihydro-2H-indol-2-ones. Dalton Trans 6 918-921... 

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