3//-Pyrrole, 3,3-dimethyl-2-phenyl

Boger DL, Panek JS et al (1992) Preparation and Diels-Alder reaction of a reactive, electron-deficient heterocyclic azadiene dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-Diazine (dimethyl 4-phenyl-l, 2-diazine-3, 6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2, 5-dicarboxylate) introduction. Organic Synth 70 335... 

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>... 

Chemical Name 6-(dimethylamino)-2- [2-(2,5-dimethyl-1-phenyl-1 H-pyrrol-3-yl)ethenyl] -1-methylquinolium salt with pamoic acid (2 1)... 

Alkyl phenyl ethers (except anisole) Dimethyl pyrroles... 

The synthesis of N-phenyl-1,3,4,6-tetrahydrothieno(3,4-c)-pyrrole-2,2-dioxide (II) was carried out by reacting aniline with 3,4-bis(bromomethyl)-2,5-dihydrothiophene-l,1-dioxide (I). The latter compound was synthesized by the bromination of the cycloaddition product, prepared from 2,3-dimethyl-l,3-butadiene and sulfur dioxide (17). 

The influence of substituents on regioselectivity was studied by using a model nitrone 3,4-dihydro-2,2-dimethyl-2/f-pyrrole 1-oxide (DMPO, 256) with different alkylidenecyclopropanes substituted with phenyl (156), electronreleasing (270 and 271) and electron-withdrawing groups (52, 272 and 4) [67,... 

Phenyl- and 2-(2-thienyl)-3,3-dimethyl-3//-pyrroles (58) were obtained by the reaction of the corresponding ketoximes 56 with acetylene catalyzed by MOH (M = Na, K) in DMSO. The reaction intermediate observed is the corresponding O-vinyl oxime 57 which undergoes [3,3] sigmatropic rearrangement and cyclization to products 58 (equation 24). The yield of the products obtained strongly depends on the structure of the ketoxime . 

Analog wird aus dem Addukt mit HCl bzw. HBr N-p-Halogenphenyl-A -pyrrolin gebildet (45). Dagegen fiihrt konzentrierte Schwefelsaure 2-Phenyl-4.5-dimethyl-3.6-dihydro-l,2-oxazin in l-Phenyl-3.4-dimethyl-pyrrol tiber 45)... 

H-Pyrrole-2,4-diamine, l-t-butyl-N2,N2-dimethyl-3-phenyl-jV4-phenylsulfonyl-X-ray, 4, 160 <78BSB893)... 

Cycloaddition reactions have been carried out with corresponding bases of Vilsmeier salts of pyrroles. Thus reaction of 153 with dimethyl acetylenedicar-boxylate gave pyrrolizines 154 and 3a-azaazulenes 155 in a nonsynchronous reaction. The structure of 3H-pyrrolizine 154a was proved by X-ray analysis.96 In a closely related reaction, pyrrolizinones 156 and 157 were obtained from the corresponding Vilsmeier salts with phenyl isocyanate.97 Reaction of 2-p-nitrobenzoylindolin-3-one (158) with methyl acetoacetate gave the benzopyrrolizinone (159).5 7... 

The synthesis of cobalt meso-diphenyl corrolates has also been reported [31]. The synthetic procedure involves the acidic condensation of 3,4-dimethyl-2-(a-hydroxybenzyl)pyrrole-5-carboxylic acid with 3,3, 4,4 -tetramethyl dipyrro-methane, followed by reaction with cobalt salts. The reaction afforded a mixture of two isomers Co(5,15-OMDPC)PPh3 and Co(5,10-OMDPC)PPh3. The formation of this latter isomer has been explained by the high tendency of self condensation of the starting pyrrole under the reaction conditions, 2-(a-hydroxybenzyl)meso-phenyl dipyrromethane can be formed. This species would afford the Co(5,10-OMDPC)PPh3 by further condensation with the dipyrromethane unit present in excess in the reaction mixture. 

Fig. 10 4-Acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-9]pyrrole 58, dimethyl 6-acetylamino-2-[3-(trifluoromethyl)phenyl]-l-benzofuran-3,4-dicarboxylate 70 [18]...

On the other hand, photogenerated closed-ring isomers of diarylethenes with pyrrole, indole, or phenyl rings, which have rather high aromatic stabilization energy, are thermally unstable.1221 The photogenerated, blue, closed-ring isomer of l,2-bis(2-cyano-l,5-dimethyl-4-pyrrolyl)perfluorocyclopentene 11a disappeared in 37 s (= t1/2 ) at 25 °C. 

An attempt by Sato17 to prepare 2-phenyl-1 -azirine from the dimethyl-hydrazone methiodide (30) resulted in the formation of 2,4-diphenyl-pyrrole (31). Although the 1-azirine may be an intermediate (see Section IV, B, 2) in this reaction, its presence could not be detected. 

A mixture of l,2-dimethyl-3-acetyl-4-isopropyl-5-phenyl pyrrole (12.75 g, 0.05 mol) and diethyl isopropylidene succinate (10.7 g, 0.05 mol) in dry toluene (70 ml) was added to a stirred solution of sodium hydride (80% dispersion in oil, 3.8 g, 0.125 mol) suspended in dry toluene (10 ml) under nitrogen atmosphere. A few drops of absolute ethanol were added to initiate the exothermic reaction. The reaction mixture was stirred for about 40 h at ambient temperature until no hydrogen was formed, and finally the reaction mixture was poured into crashed ice-water (100 ml). The organic layer was separated and extracted with saturated sodium carbonate solution (2 x 50 ml). The combined aqueous layer was extracted with toluene (50 ml), and then the aqueous phase was acidified slowly with 5 M hydrochloric acid and washed with toluene (3 x 100 ml). The toluene solution was dried with MgSO 4 and the solvent was removed the half-ester was obtained as a gum. 

Gas-phase pyrolysis of 3-(177-pyrrol-2-yl)prop-2-en-l-ol 25 (R= H) (650°C, lO -lO Torr) and [2-(l//-pyrrol-2-yl)phenyl]methanol 27 (700 °C, 10 Torr) causes loss of water and cyclization to give 3//-pyrrolizines 26 (Equation 2) and 28 (Scheme 9) in 66-95% yield <1999J(P1)2049>. At 650 °C, a number of unidentified by-products were present in the pyrolysate from the tertiary alcohol 25 (R = Me), but 3,3-dimethyl-3//-pyrrolizine 26 was obtained in satisfactory yield and purity (64% after distillation) when pyrolysis was carried out at 550 °C. 

Azaindoles are readily acylated on the pyrrole nitrogen by warming on a water bath with acid anhydrides or with acid chlorides in the presence of carbonate or pyridine. Good yields were obtained by this procedure for the following compounds l-acetyl-7-azaindole, 1-benzoyl- and l-benzenesulfonyl-7-azaindole, l-benzoyl-2-methyl-7-azaindole, 1-ethoxycarbonyl- and l-chloroacetyl-7-azaindole, l-acetyl-3-cyano-7-azaindole, 1-benzoyl-4-azindole, and 1-acetyl- and l-benzoyl-2,5-dimethyl-4-azaindole. The only reported failure was with 5-methyl-2-phenyl-4-azaindole, which failed to react with acetic anhydride or benzoyl chloride. 2-Methyl-7-azaindole-3-acetic acid was acylated by treatment of its ierGbutyl ester with sodium hydride in dimethylformamide, followed by p-chlorobenzoyl chloride. ... 

MePTZ = lO-methylphenothiazine 2,3-dpp = 2,3-bis (2-pyridyl)pyrazine 2,9-Me2-4,7-Ph2-phen = 2,9-dimethyl-4,7-diphenyl-l,10-phenanthrolme 2,9-Me2-phen = 2,9-dimethyl-1,10-phenanthroline 3,4,7,8-Me4-phen = 3,4,7,8-tet-ramethy 1-1,10-phenanthroline 4,4 - NH2 2-bpy = 4,4 -dia-mino-2,2 -bipyridine 4,4 -Me2-bpy = 4,4 -dimethyl-2,2 -bipyridine 4, 4 -Ph2-bpy = 4,4 -diphenyl-2,2 -bipyridine 4, 4 - Bu2-bpy = 4,4 -di-tert-butyl-2,2 -bipyridine 4,7-Me2-phen = 4,7-dimethyl-l,10-phenanthroline 4-MeOPh-HPh bpy = 4 -(4-methoxyphenyl)-6 -phenyl-2,2 -bipyridine 4-Me-phen = 4-methyl-1,10-phenanthroline 5,6-Me2-phen = 5,6-dimethyl-l,10-phenanthroline 5-Ph-phen = 5-phenyl-1,10-phenanthroline bimy = benzimidazol-2-ylidene biq = 2,2 -biquinoline bpy = 2,2 -bipyridine bpy-dvb-bpy = 1,4-bis[2-(4 -methyl-2,2 -bipyrid-4-yl)ethenyl]benzene bpy-pyrl = 4-(2-pyrrol-l-ylethyl)-4 -methyl-2,2 -bipyridine bpy-pyr2 = 4,4 -bis((3-pyrrol-l-ylpropyloxy)carbonyl)-2,2 -bipyridine BSA = bovine serum albumin BTA = bis(trimethylsilyl)acetylene chrysi = 5,6-chrysenequinone diimine COD = 1,5-cyclooctadiene DAB = 1,4-diaza-1,3-butadiene DFT = density functional theory dmb =1,8-diisocyano-/ -menthane dmb-tol = 4-methyl-4 -(iV-methyl-/ -tolylaminomethyl)-2,2 -bipyridine dmpe = l,2-bis(di-methylphosphino)ethane dmpm = bis(dimethylphosphino) methane dpmp = bis(diphenylphosphinomethyl)phenylphos-phine dppb = l,2-bis(diphenylphosphino)benzene dppe = l,2-bis(diphenylphosphino)ethane dpp-HCNN = 2,9-di-... 

Pyrrol 2-(Ethoxycarbonylamino-thiocarbonyl)- E5, 1228/E4, 250 (ROOC-NCO + Pyrrol) Sulfimid S,S-Dimethyl-N-(4-nitro-phenyl)- Ell, 895 (R2S + Amin) Sulfinsaure... 

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