Pyrroles 2-phenyl

Phenyl-2-pyridinylmethanone Phenyl-4-pyridinylmethanone 1-Phenyl-1H-pyrrole 2-Phenyl-l/t-pyrrole l-Phenyl 1/V-pyrrole-2,5-dione 1-Phenylpyrrolidine... 

Pyrrole, 1,2,3,4,5-pentamethyl-benzoylation, 4, 220 Pyrrole, 2,3,3,4,5-pentamethyl-reactions, 4, 83 Pyrrole, 1-pentyl-mass spectra, 4, 21-22 Pyrrole, phenyl-benzoyl oxidation, 4, 260 conformation, 4, 192... 

N-phenylmaleimide. The formation of 2-phenacylidene-3-methyl-5-phenyl-l,3-oxazoline by the treatment of the salt (158) with sodium hydride in DMSO was considered to proceed through the thiocarbonyl ylide (159). However, the thiocarbonyl ylide (160), which in a similar manner to that mentioned above was generated from its corresponding dithiolanium salt, instead underwent a spontaneous ring-closure, yielding the spiro-compound (161). The thiocarbonyl ylide dipolar characteristics of phenyl-substituted thieno[3,4-c]pyrroles, phenyl-substituted thieno[3,4-c]thiophens, and the thieno[3,4-/)benzo[c]thiophen (162) have been substantiated by their reactions with dipolarophiles. The first representative (164) of the hitherto... 

Ethyl-4-methyl-l-(phenylsulfonyl)indole 4-Ethyl-7-methyl-l-phenylsulfonyl-l,5-dihydropyrano-[3,4-b]pyrrol-5-one phenyl vinyl sulfoxide 60 [3]... 

AJ-Vlayl polymers may be used for the preparation of semiconductors (qv). Derivatives of others have biological activity, eg, a derivative of 2-phenyl-1-vinylpyrrole, 2-phen54-l-(proparg54oxyethyl)pyrrole, stimulates motor activity andiacreases excitation, etc (42) (see Vinyl polymers, M-vinyl amides). 

The light-induced rearrangement of 2-phenyl- to 3-phenyl-thiophene may occur by a similar mechanism an equilibrium between the bicyclic intermediate (26) and the cyclopro-penylthioaldehyde (27) has been suggested (Scheme 2). The formation of IV-substituted pyrroles on irradiation of either furans or thiophenes in the presence of a primary amine supports this suggestion (Scheme 3). Irradiation of 2-phenylselenophene yields, in addition to 3-phenylselenophene, the enyne PhC=C—CH=CH2 and selenium. Photolysis of 2-phenyltellurophene furnishes solely the enyne and tellurium (76JOM(108)183). 

Treatment of pyrrole, 1-methyl-, 1-benzyl- and 1-phenyl-pyrrole with one mole of A -bromosuccinimide in THF results in the regiospecific formation of 2-bromopyrroles. Chlorination with IV-chlorosuccinimide is less selective (8UOC2221). Bromination of pyrrole with bromine in acetic acid gives 2,3,4,5-tetrabromopyrrole and iodination with iodine in aqueous potassium iodide yields the corresponding tetraiodo compound. 

Azirines react with enolate anions. Initial nucleophilic attack on phenyl 1-azirine by the enolate anion derived from acetophenone gives intermediate (223) which undergoes 1,2-bond cleavage, cyclization and hydroxyl group elimination to give pyrrole (226). 

X-ray, 4, 160 (79AX(B)2228> lH-Pyrrole-2,4-diamine, 1-t-butyl-JV, JV -dimethyl-3-phenyl-JV -phenylsulfonyl-X-ray, 4, 160 (78BSB893) lH-Pyrrole-3-methanol, 4-acetyl-X-ray, 4, 160 (78AX(B)1248> lH-Pyrrole-3-methanol, 4-acetyl-, hydrate X-ray, 4, 160 (78AX(B)1248> lH-Pyrrole-3-propanoic acid, ester C NMR, 4, 172 (74JCS(P2)1004>... 

UV, 6, 1032 (74JA4268) 47/-Thieno[3,4-c]pyrrol-5-ium-4-ide, 5-methyl-UV, 6, 1032 (74JA4268) 47/-Thieno[3,4-c]pyiTol-5-ium-4-ide, 5-phenyl-UV, 6, 1032 (74JA1817) l-(2-Thienyl)ethyl acetate kinetic data, 4, 952 (77AHC(21)119>... 

Pyrrole-2,3-dialdehyde, 1-methyl-pyrrolopyridazine synthesis from, 4, 517 Pyrrole-2,5-dicarboxylic acid, 3,4-dihydroxy-l-phenyl-diethyl ester... 

The BOC group has been introduced onto the imidazole nitrogen of histidine with BOCF (pH 7-8), BOCN3, MgO, and (B0C)20. ° It can be introduced onto pyrroles and indoles with phenyl /-butyl carbonate and NaH, 67-91% yield, or with NaH, BOCN3. ... 

The aldehyde functionality present in 3-phenyl-2H-azirine-2-carbox-aldehyde reacts selectively with amines and with Qrignard and Wittig reagents to give a variety of substituted azirines. These azirines have been used, in turn, to prepare a wide assortment of heterocyclic rings such as oxazoles, imidazoles, pyrazoles, pyrroles, and benzazepins. ... 

Knorr reported the first pyrazole derivative in 1883. The reaction of phenyl hydrazine and ethylacetoacetate resulted in a novel stmcture identified in 1887 as l-phenyl-3-methy 1-5-pyrazolone 9. His interest in antipyretic compounds led him to test these derivatives for antipyretic activity which led to the discovery of antipyrine 10. He introduced the name pyrazole for these compounds to denote that the nucleus was derived from the pyrrole by replacement of a carbon with a nitrogen. He subsequnently prepared many pyrazole analogs, particularly compounds derived from the readily available phenyl hydrazine. The unsubstituted pyrazole wasn t prepared until 1889 by decarboxylation of liT-pyrazole-3,4,5-tricarboxylic acid. ... 

Ciamician-Dennstedt reaction on pyrrole, as well as pyrazoles, indoles, and Phenyl(trichloromethyl)mercury has been used as a dichlorocarbene... 

In a similar manner, metapyridophanes 18 can be prepared by reaction of sodium trichloroacetate with pyrrole 17 (Scheme 8.3.5). The transformation can also be achieved with phenyl(bromodichloromethyl)mercury, albeit in lower yield. 

The copper-catalyzed decomposition of diazoacetic ester in the presence of pyrrole was first described in 1899 and later investigated in more detail by Nenitzescu and Solomonica. Ethyl pyrrole-2-acetate (13), the normal product of electrophilic substitution, was obtained in 50% yield and was degraded to 2-methylpyrrole. Similarly iV -methylpyrrole with two moles of diazoacetic ester gave, after hydrolysis, the 2,5-diacetic acid (14) while 2,3,5-trimethylpyrrole gave, after degradation, 2,3,4,5-tetramethylpyrrole by substitution of ethoxycarbonylcarbene at the less favored )3-position. Nenitzescu and Solomonica also successfully treated pyrroles with phenyl-... 

A considerable extension of that method was reached by the condensation of 1,2- and 1,3-dithiolium- 1,3-thiaselenium- and 1,2,4-thiadiazolium salts with pyrroles, 2- or 4-phenyl- 2,4-diphenyl- and 4,5-diphenyl imidazoles (70TL481). At room temperature and in acetonitrile solution some of... 

Cation (14) leads straightforwardly to tripyrrole, by way of protonated pyrrole dimer (18), the structure of which corresponds with the structures proved for 2-methyl- and 2-phenyl-pyrrole dimers. 

Mainly C-substituted pyrroles have been synthesized by application of the Knorr pyrrole synthesis however N-substituted pyrroles can also be prepared, when starting with secondary aminoketones, e.g. bearing an N-methyl or N-phenyl substituent. 

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