Phenyl 1,10-phenanthroline

Fe(5-methyl-l,10-phenanthroline) +eC H2SO4 Fe(5 -phenyl-1,10-phenanthroline) —> 1.08 52Bra... 

OTf Pc pda Ph phen phenba triflate = trifluoromethanesulfonate phthalocyanato(2 -) 1,2-pheny lenediaminato(2 -) phenyl 1,10-phenanthroline NJV -l, 2-phenylenebis[2-acetyl-l -amino-1 -buten-3-onato( 1 -)]... 

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-... 

Phen phenanthrollne, 4-methoxy phenanthroline, 2-methyl phenanthroline, 4-methyl phenanthroline, 9-phenyl phenanthroline Miscellaneous 2,2-bipyridine, 8-qulnolinol, IDAA, MIDA, EDTA, dlplvaloylmethane... 

Sigel and co-workers" investigated the interaction between the aromatic rings of phenyl carboxylates (Ph-(CFl2)n-C02) and 1,10-phenanthroline in ternary copper(II) complexes. Variation of the number of methylene units between the aromatic ring and the carboxylate group (n=0-5) revealed that the arene - arene interaction is most pronounced for n=l. This interaction is more efficient in a 60% 1,4-... 

Reductive carbonylation of nitro compounds is catalyzed by various Pd catalysts. Phenyl isocyanate (93) is produced by the PdCl2-catalyzed reductive carbonylation (deoxygenation) of nitrobenzene with CO, probably via nitrene formation. Extensive studies have been carried out to develop the phosgene-free commercial process for phenyl isocyanate production from nitroben-zene[76]. Effects of various additives such as phenanthroline have been stu-died[77-79]. The co-catalysts of montmorillonite-bipyridylpalladium acetate and Ru3(CO) 2 are used for the reductive carbonylation oLnitroarenes[80,81]. Extensive studies on the reaction in alcohol to form the A -phenylurethane 94 have also been carried out[82-87]. Reaction of nitrobenzene with CO in the presence of aniline affords diphenylurea (95)[88]. 

Abbreviations acac, acetylacetonate Aik, alkyl AN, acetonitrile bpy, 2,2 -bipyridine Bu, butyl cod, 1,5- or 1,4-cyclooctadiene coe, cyclooctene cot, cyclooctatetraene Cp, cyclopentadienyl Cp, pentamethylcyclopenladienyl Cy, cyclohexyl dme, 1,2-dimethoxyethane dpe, bis(diphenyl-phosphino)ethane dppen, cis-l,2-bis(di[Atenylphosphino)ethylene dppm, bis(diphenylphosphino) methane dppp, l,3-bis(diphenylphosphino)propane eda,ethylenediamine Et,ethyl Hal,halide Hpz, pyrazole HPz, variously substituted pyrazoles Hpz, 3,5-dimethylpyrazole Me, methyl Mes, mesityl nbd, notboma-2,5-diene OBor, (lS)-endo-(-)-bomoxy Ph, phenyl phen, LlO-phenanthroline Pr, f opyl py, pyridine pz, pyrazolate Pz, variously substituted pyrazolates pz, 3,5-dimethylpyrazolate solv, solvent tfb, tetrafluorobenzo(5,6]bicyclo(2.2.2]octa-2,5,7-triene (tetrafluorobenzobanelene) THE, tetrahydrofuran tht, tetrahydrothicphene Tol, tolyl. 

Ethyl 6-methyl-4-phenyl-2-(phenylthio)-l,4-dihydropyrimidine-5-carboxyla-te was easily synthesized from ethyl 6-methyl-4-phenyl-2-thioxo- 1,2,3,4-tetra-hydropyrimidine-5-carboxylate and phenylboronic acid via microwave-assisted Cu-mediated S-phenylation (Scheme 108) [107]. The reaction involves the use of a stoichiometric amount of Cu(OAc)2 and a two-fold excess of 1,10-phenanthroline as a hgand. 

A stopped flow technique coupled with spectrophotometric analysis of the iron (II) complex formed has been used to investigate - the reactions of some organic complexes of iron(III) with the ion Fe ". The iron(III) was complexed with 1,10-phenanthroline, various substituted 1,10-phenanthrolines (5-methyl-, 5-nitro-, 5-chloro-, 5-phenyl-, 5,6-dimethyl-, 4,7-diphenyl-, and 3,4,7,8-tetramethyl-) and 2,2 -dipyridine, 4,4 -dimethyl-2,2 -dipyridine, and 2,2, 2"-tripyridine. The wavelengths used for the analysis lay in the region 500-552 m/i. 

The treatment of gold(III) complexes with the rigid bidentate ligand phen allows the synthesis of pseudo-pentacoordinate gold(III) derivatives. This is the case of [Au(dmp)(phen)PPh3](BF4)2 (288) (dmp = 2-(dimethylaminomethyl)phenyl)1699 or [AuCl(C4Ph4)(phen)].16 2 The donor atoms of the phenanthroline ligand occupy one equatorial and the axial position of a square pyramid with distances 2.154(8)A and 2.627(10)A in (288). 

Condensation of l,0-phenanthroline-2-carbaldehyde with a series of primary amines produces terimine systems in which the field can be varied in relatively small steps, leading to a continuous spin transition in the [Fe N6]2+ complex of the system obtained from the bulky t-butylimine 68 [107]. Similarly hydrazones may be obtained, the most important of which, in the present context, is the phenyl-hydrazone 69 (phy) [108]. 

The thermal cyclization of m-phenylenediamine derivatives (799) by heating in diphenyl ether afforded angular l,7-phenanthroline-3,9-dicarboxylate (800), if a substituent was not present at position 2 of the phenyl ring of 799 (R = H), but the linear pyrido[3,2-g]quinolinecarbox-ylate (801, R = Me, R1 = R2 = H) was prepared from the 2-methyl-substituted derivative (799, R = Me, R1 = R2 = H) (72GEP2220294). 

A study of the regioselectivity of the 1,3-dipolar cycloaddition of aliphatic nitrile oxides with cinnamic acid esters has been published. AMI MO studies on the gas-phase 1,3-dipolar cycloaddition of 1,2,4-triazepine and formonitrile oxide show that the mechanism leading to the most stable adduct is concerted. An ab initio study of the regiochemistry of 1,3-dipolar cycloadditions of diazomethane and formonitrile oxide with ethene, propene, and methyl vinyl ether has been presented. The 1,3-dipolar cycloaddition of mesitonitrile oxide with 4,7-phenanthroline yields both mono-and bis-adducts. Alkynyl(phenyl)iodonium triflates undergo 2 - - 3-cycloaddition with ethyl diazoacetate, Ai-f-butyl-a-phenyl nitrone and f-butyl nitrile oxide to produce substituted pyrroles, dihydroisoxazoles, and isoxazoles respectively." 2/3-Vinyl-franwoctahydro-l,3-benzoxazine (43) undergoes 1,3-dipolar cycloaddition with nitrile oxides with high diastereoselectivity (90% de) (Scheme IS)." " ... 

Electro-optical modulators are other examples whose efficiency is enhanced in the presence of ion-radicals. These devices are based on the sandwich-type electrode structures containing organic layers as the electron/hole-injecting layers at the interface between the electrode and the emitter layer. The presence of ion-radicals lowers the barrier height for the electron or hole injection. Anion-radicals (e.g., anion-radicals from 4,7-diphenyl-l,10-phenanthroline—Kido and Matsumoto 1998 from tetra (arylethynyl) cyclooctatetraenes—Lu et al. 2000 from bis (1-octylamino) perylene-3,4 9,10-bis (dicarboximide)s— Ahrens et al. 2006) or cation-radicals (e.g., cation-radicals from a-sexithienyl—Kurata et al. 1998 l,l-diphenyl-2-[phenyl-4-A/,A- /i(4 -methylphenyl)] ethylene— Umeda et al. 1990, 2000), all of them are electron or hole carriers. 

When compared to phenyl lithium, the addition of 2,6-dimethoxyphenyl lithium to 1,10-phenanthroline is more difficult [22]. But even the introduction of non-hindered lithium organic compounds to 2-phenylpyridine gives only small yields (a) Gilman H, Edwards JT (1953) Can J Chem 31 457 (b) Overterger CG, Lombardino JG, Hiskey R (1957) J Am Chem Soc 79 6430... 

Il)cycles formed with 2,2 -bipyridine or 1,10-phenanthroline type ligands to give a variety of target compounds (Scheme 18). These syntheses are more feasible than previous, where the complexes cis-[RuCl2(bpy)2] or fRuCl .(tpy)] have been used to cyclometalate 2-phenyl-pyridine and its derivatives (230-233). A bunch of diverse compounds have been prepared in good yields. Crystal structures of some of them are shown in Fig. 21 and their useful properties are summarized in Table IX. 

Several compounds and their derivatives that do not contain adjacent hydroxy groups on a phenyl ring have recently been identified as HIV integrase inhibitors. These include suramin (X), curcumin (XI), phenanthroline-Cu+ complexes (XII), and 3 -azido-3 -deoxythymidylate (AZT) monophosphate (XIII). 

Applications of the Conrad-Limpach reaction to the synthesis of 1-hydroxy-4,7-phenanthrolines or, more correctly, l-oxo-l,4-dihydro-4,7-phenanthrolines, from p-phenylenediamine or 6-aminoquinolines continue to be reported. l,10-Dihydroxy-3,8-dimethyl-4,7-phenanthroline has again been prepared from p-phenylenediamine,234 hot diphenyl ether being used to effect the cyclization. Other examples include the new or improved preparations of l-hydroxy-3-methyl-, 10-amino-l-hydroxy-3-methyl-,232 2-(y-chlorocrotonyl)- l,10-dihydroxy-3,8-dimethyl-, and 2,9-bis (y- chlorocrotonyl)-1,10- dihydroxy - 3,8 - dimethyl - 4,7 - phenanthro-lines.235 Compounds prepared in this way have been patented as antiasthmatic agents.178 A closely related synthesis employing poly-phosphoric acid as cyclizing agent has yielded l-hydroxy-3-phenyl-4,7-phenanthroline.236... 

Diphenyl-1,10-phenanthroline and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline give disulfonic acids on reaction with chloro-sulfonic acid at 25°. The position of substitution was not established, but presumably it occurs in the two phenyl rings.281 An improved method of sulfonation utilizes hot fuming sulfuric acid.282... 

Although 1,10-phenanthroline could not be induced to react with phenyl lithium, 4,7-dimethyl- and 4,7-diphenyl-1,10-phenanthrolines, as expected, afford the 4,7-dimethyl-2,9-diphenyl and 2,4,7,9-tetraphenyl derivatives, respectively.196... 

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