2,2 -Dimethyl-4,4 -biquinoline

Dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid Di-Me ester, in D-70208 2,2 -Dimethyl-4,4 -biquinoline, D-60413... 

Photodehydrogenation reactions may lead to dimerization or cycli-zation. Intermolecular dehydrogenation with ultraviolet light has been recently illustrated in the formation of 2,2 - bipyridine, 6,6 -dimethyl-2,2 -bipyridine, and 2,2 -biquinoline on irradiation of pyridine, a-pico-line, and quinoline, respectively, under nitrogen in cooled quartz tubes.216... 

The formation of five-coordinate gold(III) has been demonstrated clearly in the complexes of 2,9-dimethyl-l,10-phenanthroline and 2,2 -biquinoline, which have the distorted square pyramidal structures (91) and (92). However, the structures of the ligands prevent square planar coordination, so that these examples are atypical.613-615 However, a related organometallic derivative, [AuCl(C4Ph4)(phen)], is known and has a similar distorted square pyramidal structure.616... 

Many noticeable examples of chiral Lewis base catalyzed allylation of carbonyl compounds have also appeared. Iseki and coworkers published a full paper on enantioselective addition of allyl- and crotyltrichlorosilanes to aliphatic aldehydes catalyzed by a chiral formamide 28 in the presence of HMPA as an additive [41]. This method was further applied to asymmetric allenylation of aliphatic aldehydes with propargyltrichlorosilane [40]. Nakajima and Hashi-moto have demonstrated the effectiveness of (S)-3,3 -dimethyl-2,2 -biquinoline N,AT-dioxide (29) as a chiral Lewis base catalyst for the allylation of aldehydes [42]. In the reaction of (fs)-enriched crotyltrichlorosilane (54 , E Z=97 3) with benzaldehyde (48), y-allylated anfi-homoallylic alcohol 55 was obtained exclusively with high ee while the corresponding syn-adduct was formed from its Z isomer 54Z (fs Z= 1 99) (Scheme 6). Catalytic amounts of chiral urea 30 also promote the asymmetric reaction in the presence of a silver(I) salt, although the enantioselectivity is low [43]. 

The photoluminescent behavior of a complex of the type Zn(diimine)(dtsq), where diimine = 2,2 -biquinoline, phen (44), or 4,7-diphenyl-2,9-dimethyl-phen (batho) and dtsq = dithiosquarate, have been reported by Gronlund et al (135). The phen and batho complexes display broad, featureless luminescence spectra in the solid state at room temperature. Upon cooling to 77 K, the emission spectrum of Zn(batho)(dtsq) resolves into three sharp peaks overlapping the broad emission feature these sharp peaks are assigned to a diimine localized ji-ji emission. The Zn(diimine)(dithiolate) solids degrade upon UV laser excitation, which has inhibited accurate lifetime measurements. 

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-... 

PPh3 triphenylphosphine phen 1, 10-phenanthroline dmp 2,9-dimethyl-l,10-phenanthroline PPhaCHa methyldiphenyl-phosphine bpy 2,2 -bipyridine biq 2,2 -biquinoline dpp 2,9-diphenyl-l,10-phenanthroline. 

Cu(NN)(No3)2 (NN = bipy, phen, 2,9-dimethyl-l,10-phen, and 3,3 -dimethylene-4,4 -dimethyI-2,2 -biquinoline) have been prepared. Copper is approximately square pyramidal in bis(theophyllinatoXdiethylenetriamine)copper(ii) the terdentate di-ethylenetriamine and N-7 of the strongly bound theophyllinate (109) define the equatorial plane and a second theophyllinate is bonded to the axial position through N-7—thus the two purines occupy very different co-ordination sites. The crystal structure of [Cu(dpt)2]2 (dptH = 1,3-diphenyltriazine) shows discrete Cu2(dpt)4 units with a syn-syn structure as in Cu"-acetate,H20 (110). ... 

The alkenylated product (5) results from reactions of 2-iodo-4-methyl-quinoline with Pd(OAc)2 as catalyst (Scheme 2). Minor amounts of homo-coupled 4,4 -dimethyl-2,2 -biquinoline accompany the reaction. Triphe-... 

The relatively vigorous reaction conditions required to effect vinyl substitution by heteroaryl halides under the influence of Pd-catalysis may lead to homo-coupling. The dominating reaction path in attempted alkenyl-ations of 4-iodopyrimidines was the formation of 4,4 -bipyrimidines (19) (Scheme 4 Section II.A.2). In reactions of 4-iodopyrimidines with a Pd-catalyst at 160°C, near-quantitative yields of the 4,4 -bipyrimidine were obtained (79CPB193). Also, in the reaction of 2-iodo-4-methylquinoline with Pd(OAc)2 as added catalyst, a major reaction path led to 4,4 -dimethyl-2,2 -biquinoline (Scheme 2 Section II.A.2.) (82CPB3647). 

P)-(+) and (S)-(—) 3,3 -dimethyl-2,2 -biquinoline N,N -dioxides 255 were obtained by resolution of the racemate via complexation with (R) or (S)-binaphthol. An X-ray of the complex allowed the assignment of the absolute configuration (97TA341,98JA6419,00CPB306,02JA4233). 

Biisoquinoline dioxide 257 and 5,5, 6,6, 7,7, 8,8 -octahydro-3,3 -dimethyl-2,2 -biquinoline N,N -dioxide 256 have been resolved and engaged in enantioselective reactions and compared with QUINOX 258 (98JA6419, 01SL1551, 02JA4233). 

Cantharidin (2,3-dimethyl-7-oxabicyclo[2,2,1 ]heptane-2,3-dicarboxylic anhydride) as an antitumor agent A retrospective review 13CMD159. Cyclometallated iridium(III) complex with 2,2 -biquinoline N-donor hgand as a c-myc G-quadruplex stabiHzer and down-regulator of c-myc oncogene expression 13CMD576. 

However, it is not only this class of compound that "fits." All compounds of the type [ZnX2(4-Rpyridine)2l (X = halogen R = alkyl or aryl group), are tetrahedral. Similarly, both of the complex cations [Cu(I)(2,2-biquinoline ] and [Cu(I)(2,9 dimethyl-1,10-phenanthroline)2] are tetrahedral. Their commonality is ten 3d electrons, seemingly not involved in the bonding and certainly not affecting the geometry. 

Nirmal et al. have synthesized biquinoline adducts (18) in high yields by the cycli-zation of [(2-chloro-3-quinolyl)methylene]methane-l,l-dicart>onitriles (16), which was provided from reaction between aldehyde (1) and malononitrile, with 3-aryl-amino-5,5-dimethyl-cyclohex-2-en-l-ones (17) under MWI catalysed by 4-(A7, N-dimethylamino)pyridine (DMAP Scheme 6.8). The synthesized compounds were screened for their antifungal and antibacterial activities [46]. 

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