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Quinolines regioselective

In the case of the 2-dimethylamino- (or 2-amino-)methylene derivatives, the products were at first thought to be pyrimido[4,5-c]isoquinolines (267), but later work with 6-(N-substituted amino)uracils assigned the structures of the products (268) as belonging to the isomeric pyrimido[4,5-f>]quinoline system (74CB2537), in agreement with the regioselection rules above. [Pg.231]

As one might expect, most of the reported cases of Camps quinoline syntheses involve reactions in which only one of the carbonyl groups is enolizable, thus eliminating the regioselectivity problem. [Pg.387]

Skraup proposed a simple mechanism involving imine formation followed by an acid-mediated cyclization. Unfortunately the observed regioselectivity is not consistent with the proposed mechanism when, for example, electron-rich aniline 4 reacts with a, 3-unsaturated aldehyde 5 to give quinoline 6. ... [Pg.488]

Bischler has suggested that anilines undergo 1,4-addition followed by dehydration which would explain the inherent regioselectivity. Mechanistic studies suggest that the reaction involves the reversible formation of diazetidinium ions 7 and there irreversible cyclization to quinolines. ... [Pg.488]

Because of the extremely low solubility of the cyclized products, only the 8-acetyl-9-X oxo-6,9-dihydrothiazolo[5,4-g]quinoline was isolated. On the other hand, 6-substituted derivatives having the same possibility to produce linearly or angularly annelated thiazoloquinolines cyclize regioselectively. [Pg.206]

Methylbenzotriazole derivatives with an aminoethylene substituent in position 4 also regioselectively produce only the angularly annelated 7-ethoxycarbonyl-6-0X0-6,9-dihydro-2-methyl-2//-triazolo[4,5-/i]quinoline 158. Under alkaline hydrolysis the ester 158 yielded the corresponding acid 159 (90CCC1038, 92FA1001). [Pg.254]

Strong effects of the catalyst on the regioselectivity have been observed in the cycloadditions of a variety of heterocyclic dienophiles. Some results of the BF3-catalyzed reactions of quinoline-5,8-dione (21) and isoquinoline-5,8-dione (22) with isoprene (2) and (E)-piperylene (3) [25], and of the cycloadditions of 4-quinolones (23a, 23b) as well as 4-benzothiopyranone (23c) with 2-piperidino-butadienes, are reported [26] in Scheme 3.8 and Equation 3.2. The most marked... [Pg.106]

Grignon-Dubois and coworkers have shown that reduction of a quinoline using zinc and acetic acid in THF gives the dimeric compound 3-177 via intermediate 3-176 (Scheme 3.47) [70J. Usually, a mixture of the syn- and anti-products is formed the substituent has some influence on the regioselectivity of the dimerization and cydization step. With R = H and R = 6-Me, only the benzazepine 3-177 were produced, by a head-to-head dimerization. [Pg.250]

Related alkyne couplings yield tricyclic quinolines via a regioselective amination/C-H functionalization pathway (Equations (104) and (105)).98... [Pg.135]

Regioselective cyclization of /V-(4-benzoyl-5-benzimidazolyl)amino-methylenemalonates (969, R = H, Me) was observed. When the cyclization was carried out in polyphosphoric acid, then 4-phenylimidazo-[4,5-/]quinoline-5-carboxylates (970) were obtained, while the thermal cyclization in diphenyl ether at 200°C, or the cyclization in a mixture of phosphoryl chloride and polyphosphoric acid afforded 4-benzoyl-8-hydroxyimidazo[5,4-g]quinoline-7-carboxylates (971) (89KFZ692). [Pg.344]

Halogenated quinolines very often nndergo nncleophilic addition with BuLi, so must be lithiated with LDA or LiTMP " The regioselectivity of their reactions parallels that of the pyridines, and similar halogen migrations are observed (Scheme 116) . ... [Pg.556]

Quiroga J, Mejia D, Insuasty B et al (2001) Regioselective synthesis of 4, 7, 8, 9-tetrahydro-2H-pyrazolo[3, 4-b]-quinolin-5(6H)-ones. Mechanism and structural analysis. Tetrahedron 57(32) 6947-6953... [Pg.195]

Bennasar et al. reported a new radical-based route for the synthesis of calothrixin B (378) (869). This synthesis starts from the 2,3-disubstituted N-Boc indole 1558 and uses a regioselective intramolecular acylation of a quinoline ring as the key step for the construction of the calothrixin pentacyclic framework. Chemoselective reaction of in s/fM-generated 3-lithio-2-bromoquinoline [from 2-bromoquinoline 1559 with LDA] with the 3-formylindole 1558 followed by triethylsilane reduction of the... [Pg.379]

Quinoline and isoquinoline react in an analogous manner with benzene in conjugated superacids (HCI-AICI3, HBr-AlBr3) to yield predominantly cis-5,1-diphenyl-5,6,7,8-tetrahydroquinoline and <7,v-6,8-diphenyl-5,6,7,8-tetrahydroisoqui-noline, respectively (75-94% yield).297 The regioselectivity observed corresponds to the most stable dicationic intermediates 73 and 74. Unsaturated imides298 exhibit similar behavior in triflic acid (Scheme 5.33). [Pg.592]


See other pages where Quinolines regioselective is mentioned: [Pg.194]    [Pg.206]    [Pg.256]    [Pg.4]    [Pg.62]    [Pg.80]    [Pg.194]    [Pg.86]    [Pg.100]    [Pg.327]    [Pg.328]    [Pg.247]    [Pg.474]    [Pg.475]    [Pg.478]    [Pg.478]    [Pg.479]    [Pg.143]    [Pg.165]    [Pg.62]    [Pg.151]    [Pg.112]    [Pg.112]    [Pg.62]    [Pg.35]    [Pg.328]    [Pg.509]    [Pg.128]    [Pg.162]    [Pg.1252]    [Pg.123]    [Pg.238]    [Pg.433]    [Pg.299]    [Pg.433]   
See also in sourсe #XX -- [ Pg.600 ]

See also in sourсe #XX -- [ Pg.8 , Pg.600 ]

See also in sourсe #XX -- [ Pg.8 , Pg.600 ]




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