Quinolines 1,2-dihydro— from

Quinolin-2-one, 3-cyano-4-hydroxy-synthesis, 2, 428 Quinolin-2-one, 3,4-dialkyl-Knorr synthesis, 2, 425 Quinolin-2-one, dihydro-Camps synthesis, 2, 418 synthesis, 2, 402 from benzazepinones, 2, 506 from indanone oxime, 2, 487 from indanones, 2, 488 by intramolecular Friedel-Crafts reactions, 2, 421... 

The directions of rotation at C and C have been arrived at from the following considerations. The deoxy-bases (II p. 443 Q = quinoline residue) obtained from cinchonine and cinchonidine are structurally identical, i but optically different, and since they must be optically identical at C and C, and C is no longer asymmetric, the difference between them (see table, p. 446) must be due to difference in direction of rotation at C , which must therefore be dextrorotatory in cinchonine and laevorotatory in cinchonidine, and this must also be true of quinidine and quinine respectively and of the corresponding dihydro-bases. The keto-bases, cinchoninone and quininone, might be expected to exist each in two pairs, since carbon atom 8 is, according to the formula (p. 442), asymmetric, but it is better represented by the tautomeric grouping —... 

Trialkyl-2,3-dihydro-l//[l,4]diazepino[2,3-/]quinolines 109, obtained from the reaction of 5,6-diaminoquinoline with ketones, on treatment with acid or under thermal conditions afforded solely the 2-methyl-3//-imidazo[4,5-/]quino-line 110. However, no change was observed when diazepinoquinolines were treated... 

Ozonolysis of 5,8,9-trihydroxy-2,3-dihydro-l//-pyrimido[l, 2-n]quinoline-3-carboxylic acid (420), obtained from isopyoverdin isolated from Pseudomonas putida BTPl by acidic hydrolysis, gave l-2,4-diaminobutyric acid, which confirmed the hypothesis that heterocyclic chromophores 1 and 4 of pyoverdin and isopyoverdin, respectively, could have the same precursor, and the configuration at C(3) should be 5 (97ZN(C)549). 

Trihydroxy-2,3-dihydro-l//-pyrimido[l,2-u]quinoline-3-car-boxylic acid and (420) and its (15)-1-carboxylic acid isomer were isolated from isopyoverdins (97ZN(C)549, 01T1019) and pyoverdins (99MI27), respectively, after acidic hydrolysis in 3 M HCl for 5 days at 110°C. 

A mixture of 26 parts of 3-carbethoxy-6,7-methylenedioxy-4-hydroxy-quinoline, 16 parts of sodium hydroxide and 50 parts of dimethylformamide is heated at 70° to 75°C for 2 hours, then 31 parts of ethyl iodide is added over 1 hour with continued heating and stirring. After an additional 3 to 4 hours of heating (at 70° to 75°C) and stirring, the mixture is diluted with 500 parts of water, refluxed for 3 to 4 hours, acidified with concentrated hydrochloric acid and filtered to yield 18 to 22 parts of 1-ethyl-1,4-dihydro-6,7-methylene-dioxy-4-oxo-3-quinoline-carboxylic acid, MP 309° to 314°C (decomposes). The analytical sample from dimethylformamide melts at 314° to 316°C (decomposes). 

Schach S, B Tshisuaka, S Fetzner, F Lingens F (1995) Quinoline 2-oxidoreductase and 2-oxo-l,2-dihydro-quinoline 5,6-dioxygenase from Comamonas testosteroni 63. The first two enzymes in quinoline and 3-methylquinoline degradation. EurJ Biochem 232 536-544. 

Phenyl-l,2,3,6-tetrahydropyrido[2,l- ][l,3]thiazino[3,2- ]quinolin-6-ones were prepared by the reaction of 2-mercapto-5-phenyl-l,4-dihydroquinolin-4-ones with 1,3-dihalopropane <1997JAK97/278780>. 7-Acetyl-2-aryl-9-cyano-6-methyl-8-phenyl-3,4-dihydro-277,877-pyrido[2,l- ][l,3]thiazin-4-ones were obtained from 5-acetyl-3-cyano-6-methyl-4-phenyl-l,2,3,4-tetrahydropyridine-2-thione with 3-aryl-2-propenoyl chloride <2002CHE761>. Reaction... 

Reaction of pyridines with dialkyl acetylenedicarboxylates in the presence of isocyanates in dry CH2C12 at room temperature produced 1-substituted 2-oxo-l,9a-dihydro-2/7-pyrido[l,2-tf]pyrimidine-3,4-dicarboxylates <2004TL1803>. One-pot, three-component synthesis of 1-substituted 2-oxo-l,llb-dihydro-2//-pyrimido[2,l- ]iso-quinoline-3,4-dicarboxylates and 4-(3-chloro-4-methylphenyl)-3-oxo-4,4a-dihydro-3/7-pyrimido[l,2-tf]quinoline-l,2-dicarboxylate was realized by the reaction of isoquinoline and quinoline with isocyanates and dialkyl acetylenedicarboxylates <2004S861>. Diastereomeric mixtures of l-tosyl-2-aryl-l,llb-dihydro-2/7-pyrimido[2,Ttf]isoquinoline-3,4-dicarboxylates were obtained from isoquinoline, iV-tosyl-benzaldehyde imines, and DMAD <2002OL3575>. 

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