Imidazo quinoline-8-carboxylates

C13H11CIN2O2 f 3-(p-Chlorophenyl)-6-methyl-2-oxo-2,3,3a,7a-tetrahyd-ro-oxazolo[4,5-b]pyridine, 45B, 403 Cl3H11CIN2O2, 3-(p-Chlorophenyl)-7a-methyl-2-oxo-2,3,3a,7a-tetrahyd-ro-oxazolo[4,5-b]pyridine, 45B, 403 C13H12N2O5, 1-Ethyl-1,4-dihydro-4-oxo-5-amino-6,7-methylenedioxy-3-quinoline-carboxylic acid, 42B, 277 C13H13CIN2O3S, 1-p-Chlorophenyl-4-(a-D-erythrofuranosyl)-4-imidazo-line-2-thione, 40B, 332... 

Derivatives of 1 -ethy l-7-alkylamino-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 137 have been reduced to corresponding diamines 138 and afterwards converted exclusively to linearly annelated imidazo[4,5-g]quinoline-7-carboxylic acid derivatives 139 (Scheme 43) (88KFZ33). 

The cyclization of (imidazo[4,5-g]quinolin-5-yl)methylenemalonate (146) by heating in polyphosphate at 130°C afforded benzimidazolo[6,5,4-/./Jquinolizine carboxylate (744) in 50% yield [79JAP(K)154797]. 

Methyl phenyl- or p-chlorophenylglycinate afforded with 4-chloroquino-line-3-carboxylate a pyrrolo[3,2-c]quinoline derivative 130 [89H(29)899]. Alkyl a-(2-quinolyl)glycinate was transformed into imidazo[l,5-a]quinoline 131 with DMF-DMA, TOF, or DEMA f91JHC1715, 91ZN(B)1110]. 

Many ring-fused imidazole derivatives have been synthesized by various methods. Domino Michael addition retro-ene reaction of 2-alkoxyiminoimidazolidines and acetylene carboxylates provided a synthesis of 2,3-dihydroimidazo[l,2-a]pyrimidin-5-(l//)-ones <05T5303>. A single step synthesis of 3,5-dialkyl-9-nitroimidazo[l,2-c]quinazolin-2(3//)-ones from simple carbonyl compounds, primary amines or amino acid methyl esters and 2-azido-5-nitrobenzonitrile has been published <05TL5778>. Diels-Alder reaction of azadienes and benzimidazole-4,7-diones afforded imidazo[4,5-g ]quinoline-4,9-dione derivatives <05EJ01903>. Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 4,5-diphenyl-l,3-dihydro-2//-imidazol-2-one provided a one-pot synthesis of 5//-imidazo[2,l-ft][l,3]oxazine derivatives <05T2645>. Microwave irradiation was employed in the synthesis of 1-ary 1-3-acetyl-1,4,5,6-... 

A series of ethyl 2-R(Ar)-9-cyclopropyl-4-fluoro-6-oxo-lH-imidazo[4,5-/i] quinoline-7-carboxylates 78 have been obtained through cyclocondensations of the corresponding 7,8-diamino qninolones [233], Also a number of tetracyclic [h]-annelated fluoroquinolones, snch as l-cyclopropyl-6-fluoro-4-oxo-l,4-dihydro-pyrido[2,3-fl]carbazole-3-carboxylic acids 79 and their thiene isosters have been obtained (Scheme 36) [198], All derivatives proved to possess a high activity against Bacillus subtilus and Staphylococci. 

Ager IR, Barnes AC, Danswan GW, Hairsine PW, Kay DP, Kennewell PD, Matharu SS, Miller P, Robson P, Rowlands DA, Tully WR, Westwood R (1988) Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,l-c][l,4]benzoxazines, imidazo[l,2-tj] quinolines, imidazo[l,2-a]quinoxalines, imidazo[l,2-a]quinoxalinones, pyirolo[l,2-tj]quinox-alinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,l-f>]benzothiazoles. J Med Chem 31 (6) 1098-1115. doi 10.1021/jm00401a009... 

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