4-Methyl-pyrazolo quinoline

Methyl-l,5-diaminopentane, 413 Methylene chloride, 17, 182, 265, 291 2-Methyleneglutaric dinitrile, 392 Methyl ethyl ketone, 260, 454 Methyl isobutyl ketone, 525 Methyl mercaptan, 240 Methyl methacrylate, 29, 254 a-Methylnadic anhydride, 452 4-(a-Methylnadimido)-benzoic acid, 452 2-Methyl-5-nitroaniline, 454 2-Methylpentamethylenediamine, 392, 393, 399, 409 A -Methyl-4-picolinium hexafluorophosphate, 157 Methylpiperidine, 399 4-Methyl-pyrazolo[3.4-b]quinoline, 37... 

Pyrazolo-based organic materials belong to the most promising blue electroluminescent and transporting materials. A series of pyrazoloquinoline derivatives have been synthesized for use in LEDs. Their optical properties can be tuned by the modification of the side groups [145]. 4-Methyl-pyrazolo[3.4-b]quinoline emits at 440-460 nm [146]. 

Pyrazolopyrimidinones C NMR, 5, 308 methylation, 5, 310 synthesis, 5, 329 Pyrazolopyrimidinones, thioxo-synthesis, 5, 324 Pyrazoloquinazolines synthesis, 5, 317, 322 Pyrazolo[ 1,5-n]quinazolines synthesis, 5, 273 Pyrazolo[ 1,5-c]quinazolines synthesis, 5, 324 Pyrazolo[2,3-n]quinazolines synthesis, 3, 378 Pyrazoloquinazolinones synthesis, 5, 342 Pyrazolo[4,3-/]quinazolinones synthesis, 5, 273 Pyrazolo[4,3-g]quinazolinones synthesis, 5, 273 Pyrazolo[3,4-/]quinolines synthesis, 5, 273 Pyrazolo[4,3-/]quinolines synthesis, 5, 273 Pyrazolo[l,5-n]quinoxalines synthesis, 5, 339 Pyrazolo[3,4-6]quinoxalines synthesis, 5, 272... 

Thermal cyclization was also the route employed to prepare 9-hydroxy-7-methyl-l/f-pyrazolo[3,4-/]quinoline (74) from the 6-aminoindazole/ethyl acetoacetate condensation adduct shown in Equation (41) <92JMC4595>. The hydroxyl substituent of compound (74) was then converted (POCl3, DMF) to a chloro, which in turn was displaced by treatment with aryl amines to give tricyclics with potent in vivo immunostimulatory activity like that noted for regioisomeric l//-imidazo[4,5-/]quinolines but unlike the inactive pyrazolo[4,3-/]quinolines. Although it was noted with some interest that none of the linear tricyclic isomer had been isolated, this finding actually parallels that reported earlier for the similar condensation of 1- and (V(6)-alkyl and unsubstituted 6-amino-indazoles with diethyl ethoxymethylenemalonate <83JHC1351>. 

Organ and co-workers [120] described a unique approach to MCRs using a microwave-assisted, continuous flow process for the synthesis of new series of tetrahydro-pyrazolo[3,4-6]quinolin-5(6//)-ones 79. An aldehyde, dimedone, and 5-amino-3-methyl-l//-pyrazole were reacted, yielding the desired compound 79 in moderate to excellent yields. It was proved that the electronic properties of the substituted benzaldehydes have an important impact on the conversions as with electron-donating groups rather low yields were obtained (Scheme 60). 

Pyrazolo[3,4-Z)]pyridines, the 7-chloro-6-fluoro-2,4-dimethylquinoline and its mercapto-thiadiazolyl or oxadiazolyl quinolines 21 were prepared via Diels-Alder reaction conversion of methyl 2-(3-oxo-3-phenylpropenylamino)benzoate into 3-benzoyl-l.S -quinolin-4-one 22 . A mixture of aniline derivatives and malonic ester gave a variety of 3-aryl-4-hydroxyquinolin-2(l//)-ones 23. Condensation of isatins with ketones afforded quinoline-4-carboxylic acids. 2-Aryl-l,2,3,4-tetrahydro-4-quinolinones 22 and carbazolylquinolone were also prepared. The substitution of 2-chloroquinoline gave the 2-substituted quinolines. Basic alumina has catalyzed the C-C bond formation between 2-hydroxy-1,4-naphthoquinone and 2-chloroquinoline derivative to give 21. Reaction of organic halides with 8-hydroxyquinolines gave the respective ethers. The azodye derivatives of 21 were prepared in the absence of solvent. Silica gel catalyzed the formation of 2-ketomethylquinolines from reaction of 2-methylquinolines with acyl chlorides. 

Copolymers from 2-(carbazol-9-yl)ethyl methacrylate and 3-phenyl-7-methacryloyloxyethoxy-l-methyl-lH-pyrazolo[3,4-b]-quinoline can be fabricated into LEDs that emit blue light. ... 

Phenyl-7-methacryloyloxyethoxy- 1-methyl-1 H-pyrazolo[3,4-b]-quinoline, 32 3-(5-Phenylpentyl)-4-methylbenzyl chloride, 70 p-Phenylphenol, 139, 284... 

Catalytic Synthesis of 3-methyl-l-phenyl-177-benzo[g]pyrazolo[3,4-5] quinoline-5,10-dione Derivatives Using Nano Cerium Oxide as... 

Scheme 3.51 Synthesis of 3-methyl-l-phenyl-l/f-benzo[ ]pyrazolo[3,4-6]quinoline-5,10-diones...

Wang et al. [49] developed a highly regioselective Povarov reaction of an aromatic aldehyde, l//-indazol-5-amine, and methyl 3-oxobutanoate catalyzed by iodine. This novel reaction selectively gave 3/f-pyrazolo[4,3-y]quinolin-9-yl acetates 20, rather than 3//-pyrazolo[4,3-/jquinoline-8-carboxylate derivatives. Further, they [50] also extended the reaction using tetrahydropy ran-4-one instead of methyl-3 -oxobutanoate for the synthesis of 7-aiylpyrano[3,4-c]pyrazolo[3,4-/]quinoline derivatives 21 (Scheme 10.16). 

The synthesis of l-methyl-l,4-dihydro-9H-pyrazolo[4,3-(i]quinoline-9-one 72, inhibitor of protein kinase C, has been performed by means of cyclization of 4-[(4-fluorophenyl)amino]-l-methyl-lH-pyrazole-5-carboxylic acid (Scheme 33) [227]. The main trends in development of research studies in the field of [b]-annelated fluoroquinolones are dealt with use of these compounds for the synthesis of novel [ij]-annelated systems, a varying of substituents at C-7, and also with obtaining of new 2-substituted fluoroquinolones. 

Kawamura K, Michara S, Nuldi S, UcMda 1 (2003) Preparation of l-methyl-l,4-dihydro-9H-pyrazolo[4,3-b]-quinoline-9-one derivatives as protein kinase C inhibitors. JP Patent 55376, 26 Feb 2003... 

D. Catarzi, L. Cecchi, V. Colotta, G. Filacchioni, C. Martini, P. Tacchi, A. Lucacchini, Tricyclic heteroaromatic systems. Synthesis and A1 and A2a adenosine binding activities of some l-aryl-l,4 dihydro-3-methyl[l]benzop)frano[2,3-c]pyrazol-4-ones, l-aryl-4,9-dihydro-3-methyl-IH-pyrazolo [3,4-fc]quinolin-4-ones, and l-aryl-lH-imidazo[4,5-fc]quinoxalines, J. Med. Chem. 38 (1995) 1330-1336. 

In the recent years, Reis et al. [38] reported synthesis and anticancer activity of 2-(benzothiazol-2-yl)-8-substituted-2H-pyrazolo[4,3]quinolin-3(5H)-ones. The in-vitro anticancer activity of the synthesized compounds revealed, methyl and bromo substitution at C-6 position of quinoline showed considerable effect against three cancer cell lines. IC50 value of 2.3 mg/mL against breast cancer (MDA-MB-435), colon (HCT-8) and central nervous system (SF-295) cell lines (IC50 values of 4.1 and 4.5 mg/mL, respectively). 

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