Fluorinations quinoline

Using Cohn s conditions fluorinated quinoline 16 was synthesized from the... 

This fluorinated quinoline antibiotic 96 has been labelled113b with 18F for biodistribution studies by PET. 

Abstract The data on the chemistry of fluorinated quinolines available in the literature of the last 10-15 years are presented. A variety of synthetic methods exploiting cyclization and cycloaddition reactions, displacements of halogen atoms or the diaza group, as well as direct fluorinations have been considered. Novel approaches to functionalization of polyfluorinated quinolines, including nucleophilic displacement of fluorine atoms, cross-coupling reactions, and synthesis on the basis of organome-tallic compounds are discussed. Selected representative examples of fluoroquinolines... 

A number of fluorinated quinolines have found application in agriculture, and also as components for liquid crystals. Cyanine dyes on the basis of quinolines also make a considerable share in commercial production. 

A growing interest in fluorinated derivatives of quinolines stimulates research smdies aimed at development of novel methods of synthesis, studying of reactivity of fluorinated quinolines and their plausible practical applications, as indicated by numerous publications, including recent monograph and review articles [1-4],... 

Scheme 2 Formation of pyridine ring of fluorinated quinolines...

The intramolecular cyclization takes place on treatment of ortfto-alkynyl substi-tnted aryl isocyanides 51 with tetrabutyl ammoninm fluoride affording the corresponding 2-fluorinated quinolines 52 in good to excellent yields (Scheme 19) [30],... 

Fluorinated Quinolines Synthesis, Properties and Applications CHjPh NH... 

Stereoselective multi-steps synthesis of fluorinated 2,3-dihydroquinolin (lH)-ones proceeding as a one-pot transformation has been described [50]. The Ts-protected 0-(2-anilino)- 0-ketoesters 75 are capable of reacting with a variety of aldehydes under mild conditions to form fluorinated quinolines 76 in good yields (up to 98 %) and high diastereo selectivities (dr up to 99 1) (Scheme 30). The compounds 76 are considered as versatile synthetic intermediates, and, indeed, they can be transformed into functionalized heterocyclic derivatives. For example, decarboxylation of compounds 76 results in the formation of 3-fluoroquinolines 77, while reduction with NaBH4 affords a-fluoro-)3-hydroxy esters 78. 

The quinoline system is of interest as an important building-block for the whole number of biologically active compounds therefore development of new synthetic routes to fluorinated quinolines, capable of various transformations is a key task of heterocyclic chemistry. One of the most common approaches to functionalization of fluoroquinolines is based on their reactions with nucleophiles. In particular,... 

Reactions, not being accompanied by the displacement of fluorine atoms are also important for functionalization of fluorinated quinolines. For instance, 6-substituted 5,7,8-trifluoroquinolines 148-153 were obtained from 6-trifluoro-methyl-5,7,8-trifluoroquinoline 147 (Scheme 67) through hydrolysis of the CF3 group in quinoline 147 followed by decarboxylation of 5,7,8-trifluoroquinoline-6-carboxylic acid 148 on heating in DMF [6]. From the acid 148 obtained is the acyl chloride 150, which gives with methanol the methyl ester 151 and with ammonia - the amide of... 

Ichikawa J, Mori T, Miyazaki H, Wada Y (2004) C-C bond formation between isocyanide and P,p-difluoroalkene moieties via electron transfer fluorinated quinoline and biquinoline syntheses. Synlett 2004(7) 1219-1222... 

Ahmad Y, Leconte J, Malpart J, Mignani S, Mutti S, Tabart M (2005) New process for preparation of 3-fluorinated quinolines. FR Patent 2862301, 20 May 2005... 

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