Quinoline-5,8-diones, synthesis

PyrimidoX4,5-6]quinoline-2-carboxylic acids synthesis, 3, 224-225 Pyrimido[4,5-6]quinoline-2,4-diones synthesis, 3, 224 Pyrimido[5,4-6]quinolinediones synthesis, 3, 219 Pyrimido[4,5-6]quinolines synthesis, 3, 219, 224, 227, 228, 230, 231 Pyrimido[4,5-c]quinolines synthesis, 3, 224, 227 tautomerism, 3, 205 Pyrimido[5,4-6]quinolines synthesis, 3, 227 Pyrimido[5,4-c]quinolines synthesis, 3, 219, 224, 227, 230 Pyrimido[5,4-6]quinoline-1,3,5-trione, 7-chloro-synthesis, 3, 221... 

Laschober, R. Stadlbauer, W. Synthesis of 3-heptyl and 3-nonyl-2,4(lH,3H)-quinoline-diones. Liebigs Ann. Chem. 1990,1083-1086. 

Edmont D, Chenault J (2003) 8-Fluoro-4-hydroxy-l//-[l,2,4]triazino[4,5-a]-quinoline-l,6(2//)"dion - synthesis and reactivity. J Heterocycl Chem 40 789-793... 

An acid-catalyzed substitution of a 6-oxo group on 2-aminopteridine-4,6-dione with hydrogen chloride in alcohols (65-100°, 3 hr, 80% yield) represents a convenient synthesis of the 6-alkoxy analogs. The reaction proceeds also with pteridine-2,4,6-trione and its 1-methyl and 1,3-dimethyl derivatives. While methoxylation of 2,4,7-trichloro-quinoline gives about equal amounts of 2- and 4-substitution, acid-catalyzed hydrolysis gives specific reaction at the 2-position only. ... 

A one-pot synthesis of pyrano[3,2-c]quinolin-2,5(<5/7)-dione 107 was reported through the condensation reaction of chlorocarbonyl ketenes 108 with 4-hydroxyquinolin-2(l//)-ones 109. This simple procedure was shown to be a convenient synthesis of pharmacologically active compounds in high yields <06S435>. 

Selig, P. and Bach, T. (2006) Photochemistry of 4-(2 -aminoethyl) quinolones enantioselective synthesis of tetracyclic tetrahydro-laH-pyrido [4, 3 2,3]-cydobuta[l,2-c] quinoline-2,11 (3H, 8H)-diones by intra- and inter-molecular [2 + 2] photocydoaddition reactions in solution. Journal of Organic Chemistry, 71, 5662—5673. 

Isatin (lH-indole-2,3-dione) is a synthetically versatile substrate, where it can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as a raw material for drug synthesis. Isatin has also been found in mammalian tissues, and its function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatin for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information. 

Selig P, Bach T (2006) Photochemistry of 4-(aminoethyl)quinolones Enantioselective synthesis of tetracyclic tctrahydro-1 af/-pyrido[4, 3 2,3]cyclo-buta[l,2-c]quinoline-2,11(377,877)-diones by intra- and intermolecular [2+2]-photocycloaddition reactions in solution. J Org Chem 71 5662-5673... 

Tu and co-workers [101] reported the synthesis of a series of novel pyrimido [5,4-6][4, 7]phenanthroline-9,11(7/7,8/7,10/7,12//)-diones 55 via a microwave-assisted three-component reaction of barbituric acid, an aldehyde and quinolin-6-amine in DMF without any catalyst. The results suggest that aldehydes bearing electron-withdrawing groups have higher reactivity providing higher yields in shorter reaction times (Scheme 41). 

Tu SJ, Jiang B, Jia RH (2006) An efficient one-pot, three-component synthesis of indeno [1, 2-b]quinoline-9, 11(6H, 10H)-dione, acridine-1, 8(2H, 5H)-dione and quinoline-3-carbo-nitrile derivatives from enaminones. Org Biomol Chem 4 3664—3668... 

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