2- Phenyl-l,3-indandiones

Halidor (l-benzyl-l-(3-dimethylarainopropoxy)cycloheptane fumarate) reduced the ulcer formation due to 16-20 days of glucose feeding in rats.°9 Restraint and serotonin ulcers were also blocked. Phenindione (2-phenyl-l,3 indandione) therapy in man was reported to have induced hemorrhagic ulcerative colitis.70... 

The ionization kinetics of 1,3-diketone carbon acids are slow relative to those of classical acids and bases. The ionization kinetics of three 4 -substituted 2-phenyl-13-indandiones, 4 -chloro-4 -methoxy-, and 2-phenyl-l,3-indandione itself, were studied at 25° and ionic strength 0.1 using stopped-flow spectrophotometry and a pH jump technique."... 

Benzyl-2-phenyl-l,3-indandione refluxed 5-10 hrs. in piperidine containing a few drops of coned. HCl -> a,/ -diphenylpropiophenone-o-carboxylic acid piperidide. Y 73.3%. F. e. s. R. Valters, A. Kipina, and G. Vanags, Latvijas PSR Zinatnu Akad. Vestis, Kim. Ser. 1963, 59 C. A. 59, 13945d. 

Phenyl-1,3-indandione heated 1.5 hrs. at 180-190° with methylene iodide in the presence of powdered K-carbonate 2-iodomethyl-2-phenyl-l,3-indandione. 

Phenolic ethers, dealkylation of, 287 Phenols, nitrosation of, 394 Phenoxypropadiene, 11 3-Phenylamino-l-butyne, 97 Phenyl azide, 281-282 Phenylazoalkanes, 327 Phenylazodiphenylphosphine oxide, 328 Phenylazoethane, 308 Phenylazohydroperoxides, 331 2-Fhenylazo-l,3-indandione, 299 Phenylazo-l-naphthalene, 304, 311 PhenyIazo-2-naphthaIene, 304, 311 Phenylazonaphthalenes, 310... 

Cyclic vinyl-A3-iodanes undergo direct a-vinylations of 1,3-dicarbonyl compounds [132]. In these reactions, the desired a-vinylations were accompanied by a-arylations as a competing side reaction thus, reaction of the potassium enolate of 2-methyl-1,3-indandione to cyclohexenyl(phenyl)-A3-iodane 22a afforded 2-cyclohexenyl-l,3-indandione in 86 % yield and 2-phenyl-1,3-indandione in... 

Because the hydrogen atom and phenyl group migrate so readily, the reactions of / -dicarbonyl enolates with ethynyl- and (phenylethynyl)iodonium salts can be expected to result in alkynylation. It has already been noted that the 2- -hexyl-l,3-indandionate ion undergoes alkynylation with (phenylethynyl)phenyliodonium tetrafluoroborate (equation 43), despite the availability of the -hexyl group for [2 + 3] annulation. Ethynylations of six / -dicarbonyl enolates and the anion of 2-nitrocyclohexane with ethynyl(phenyl)-iodonium tetrafluoroborate in THF have also been reported27. For example, admixture of the ethynyliodonium salt and the anion of ethyl 2-cyclopentanone-l-carboxylate in THF affords the 1-ethynyl derivative in 71% isolated yield (equation 124)27. 

Apart from copper(I)-mediated reactions, few studies of the treatment of vinyliodonium salts with carbanions have appeared. The vinylations of the 2-phenyl- and 2- -hexyl-l,3-indandionate ions shown in equations 222 and 223 are the only reported examples of vinyliodonium-enolate reactions known to this author26,126. ( ,)-l-Dichloroiodo-2-chloroethene has been employed with aryl- and heteroarvllithium reagents for the synthesis of symmetrical diaryliodonium salts (equation 224)149,150. These transformations are thought to occur via the sequential displacement of both chloride ions with ArLi to give diaryl (/ -chlorovinyl)iodanes which then decompose with loss of acetylene (equation 225). That aryl(/ -chlorovinyl)iodonium chlorides are viable intermediates in such reactions has been shown by the conversion of ( )-(/ chlorovinyl)phenyliodonium chloride to diaryliodonium salts with 2-naphthyl- and 2-thienyllithium (equation 226)149,150. 

Sodio-2-phenyl-l,3- indandionc Ph IPh+Cl- r-BuOH 017 r.t. 2-Phenyl-2-pheny lethynyl-1,3-indandione (73) 312... 

An ethanolic soln. of 2-benzoyl-l,3-indandione added dropwise during 2 hrs. to a refluxing mixture of ethylenediamine, some formic acid, and ethanol, the product isolated after 18 hrs. reflux 2,3-dihydro-5-phenyl-6H-indeno[l,2-e][l,4]diazepin-6-one. Y 75%. F. e. and reactions s. W. A. Mosher and S. Piesch, J. Org. Chem. 35, 1026 (1970). 

Phenyl-2-nitro-l,3-indandione added to a soln. of Na and phenol in acetone, and shaken 2 min. until dissolved 3-a-nitrobenzylidenephthalide. Y 74%. F. e. 

Phenyl-1,3-indandione added to a soln. of Na in ferf-butanol, then phenyl-(y -phenylethynyl) iodonium chloride added at room temp, with stirring under Ng, and gently refluxed 5-10 min. 2-phenyl-2-phenylethynyl-l,3-indandione. Y 73%. F. e. s. F. M. Beringer and S. A. Gallon, J. Org. Ghem. 30, 1930 (1965). 

Synonyms 2(( -chlorophenyl)phenylacetyl)-l f-indene-l,3(2//)dione 2-((p-chloro-phenyl)phenylacetyl)-1,3 -indandione Lip-hadione Afnor Topitox Ranac... 

A. Molinelli, R. Weiss and B. Mizaikoflf, J. Agric. Food Chem., 2002, 50,1804. The photoreactivity of 3HF has been investigated in the past, and it is mostly focalized on the photochemical rearrangement (under anaerobic conditions) to afford 3-hydroxy-3-phenyl-l,2-indandione and to the photo-oxygenation that mainly occurs in apolar media, see for instance S. L. Studer, W. E. Brewer, M. L. Martinez, P. T. Chou, J. Am. Chem. Soc., 1989, 111, 7643 I. Yokoe,... 

Diphenyl-l,2-indandione (23) yields 9-phenyl- 10-anthrone when irradiated in benzene solution.88 One possible rationalization of the observed product is shown. 

---