Quinoline 2-phenyl

Preparation of 8-Methyl-2-phenyl-quinoline-4-carboxylic acid (32)... 

On boiling the methiodide with 70% sulfuric acid an N-methyl-oxo derivative was obtained, and this in turn gave 3-amino-2-phenyl-quinoline, methylamine, and ammonia on fusion with soda lime. The bulk of the evidence therefore favors quaternization at N-2 (cf, 154), in which case the acid-hydrolysis product is 155. Quaternization at N-2 would be expected because of the steric influence of the 10-phenyl group and the influence of the 4-amino group (cf. 4-hydroxy-pyridazine ) in the pyridazine-type ring, although the partial double-bond character of that ring is probably different from that in pyridazine itself. 

Bromoquinolines behave in the Suzuki reaction similarly to simple carbocyclic aryl bromides and the reaction is straightforward. Examples include 3-(3-pyridyl)quinoline (72) from 3-bromoquinoline (70) and 3-pyridylboronic acid (71) (91JOC6787) and 3-phenyl-quinoline 75 from substituted 3,7-dibromoquinoline 73 and (2-pivaloylaminophenyl)boronic acid 74 (95SC4011). Notice that the combination of potassium carbonate and ethanol resulted in debromination at the C(7) position (but the... 

AX(C)1119>, 3-(2 -phenyl-quinolin-4 -yl)-[l,2,4]triazolo[3,4-Albenzothiazole 7 <2002JlST41, 2001MI2>,... 

The mechanisms of aminolysis of substituted phenyl quinoline-8- and -6-carboxylates, (36) and (37), have been evaluated using AMI semiempirical and HF/6-31- -G(d) ab initio quanmm mechanical methods to study the ammonolyses of the model systems vinyl c/x-3-(methyleneamino)acrylate (38), c/x-2-hydroxyvinyl di-3-(methyleneamino)acrylate (39) and vinyl rranx-3-(methyleneamino)acrylate (40). Both experimental and computational results support the formation of a tetrahedral intermediate in the reaction. The results of this study are fully consistent with the experimental observations for the aminolyses of variously substituted phenyl quinoline-8- (36) and -6-carboxylates (37). ... 

Autoxidation of indoles under basic conditions leads to the chemiluminescent ring cleavage of the heterocyclic ring (65MI30500, 65MI30501, 66CC522) which, in the case of 3-methylindole, can lead to a subsequent base-catalyzed formation of 2-(2-amino-phenyl)quinoline (77H(8)743>. 

The 3-dimethylamino-2-phenyl-allylideneaniIines (225a-e) cyclize to 3-phenyl-quinolines (227) and as expected (225 c-e) derived from meta-substituted anilines, yield mixtures of the 5- and 7-substituted quinolines (227c-e) ... 

A mixture of 2-amino-5-chlorobenzophenone, acetic acid, and polyphosphoric acid heated 15 min. at 140-145° 2-(2-benzoyl-4-chloranilino)-6-chloro-4-phenyl-quinoline. Y 89%. F. e., also with 2 different o-aminoketones via intermediates, s. T. Ishikawa et al.. Bull. Chem. Soc. Japan 45, 1839 (1970). 

Self-assembly of rod-coil-rod block copolymers based on novel polyCquinoline-styrene-quinoline) triblocks have been prepared as well. The presence of a poly(phenyl quinoline) block, which is a Ji-conjugated system, makes these materials suitable for electronic, optoelectronic, and photonic applications (Chen and Jenekhe 2000). 

In view of the addition of phenyllithium to the 1,2-position of 2-phenyl-quinoline (52) the identity of the dibenzylquinoline might be questioned... 

ITC) deposited on flexible, plastic substrates such as PMMA or polycarbonate was used as the conductive electrode substrate, with the active electrochromic electrodes producible as a roll which could be attached to window panes with common (e.g. cyanoacrylate) adhesives. This device again optionally used a counter electrode which was also electrochromic, with the difference that it could be not only a metal oxide such as WO3, but also, interestingly, an n-type CP, which of course displays electrochromism which is complementary to that of the more common p-type CPs. Thus, as cathode materials, the p-type CPs P(ANi) s, P(Py) s and poly(phenylene vinylene) were listed as usable, with virtually all the common dopants. As anode materials, WO3, M0O3, poly(isothianaphthene), and the -type CPs poly(alkoxy-thienylene vinylene) poly(p-phenylene), poly(phenyl quinoline) and poly(acetylene) were listed as usable. Liquid nonaqueous electrolytes based on common solvents such as DMSO and THF were used. No electrochromic data were however given in the patent or in subsequent publications. 

Polyquinolines represent another class of photocon-ductive 7r-conjugated rigid-rod polymers. High molecular weight polyquinolines (M 5 x 10 ) are prepared by an acid catalyzed reaction of aromatic o-amino ketones with keto methylene compounds [468,469]. Stolka and co-workers [470] recently reported on steady state photoconductivity measurements in poly(2,2 -(biphenylene)-6,6 -bis(4-phenyl quinoline)) (73b). In both polymers like in other conjugated polymers the low energy threshold of... 

The bis(naphthoquinones) la, b were obtained by published methods . Bis(2,3-bromomethyl)1,4-naphthoquinone 2 was donated by Professor W.K. Musker, University of California, Davis. Antitumor agent 6 (Dup 785) was procured from E.I. DuPont Pharmaceuticals. Samples 7a, b and 2-phenyl-quinoline (Aldrich Chemical Company) were used without further purification. Amide 7c was prepared from the acid by standard methods, m.p. 197-198 C, lit. m.p. 199 C. Camptothecin 8 was acquired from Dr. Monroe Wall, Research Triangle Institute. 

Quinoline has previously been reported to reduce at -0.86 V (corrected to NHE) in an aqueous pH 4 buffer . The more positive value for 2-phenyl-quinoline reflects the effect of conjugation. 

Bruice, P.Y., Bruice, T.C. Intramolecular general base catalyzed hydrolysis and tertiary amine nucleophilic attack vs. general base catalyzed hydrolysis of substituted phenyl quinoline-8- and -6-carboxylates. J. Am. Chem. Soc. 1974, 96(17), 5523-5532. 

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