A versatile new synthesis of quinolines and related fused pyridines. Part 9. Synthetic application of the 2-chloroquinoline-3-carbaldehydes

Meth‐Cohn, Otto; Narine, Bramha; Tarnowski, Brian; Hayes, Roy; KEYZAD, A.; Rhouati, Salah; Robinson, A.

doi:10.1039/p19810002509

Cited by 62 publications

(24 citation statements)

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“…The precipitate was filtered, washed with water, and dried to give Chloroquinoline-3-carbaldehyde (7b). A. Enediamine 3 (1.02 g, 7.8 mmol) was added to a solution of compound 7b [7] (0.72 g, 3.7 mmol) in dry DMF (10 ml) and left for 4 days at room temperature. Solvent was evaporated at 40ºC at reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

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Competitive formation of condensed azines and dihydropyridines in the reaction of ethyl 3,3-diaminoacrylate with o-halo carbaldehydes

Eliseev

Dar’in

Селиванов

et al. 2008

Chem Heterocycl Comp

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The reaction of ethyl 3,3-diaminoacrylate with quinoline-3-carbaldehydes and 3-nitrobenzaldehydes to give a dihydropyridine and condensed azine has been studied with respect to the number and reactivity of the halogen atoms in an ortho position to the formyl groups. For the series of quinoline-3-carbaldehydes it was found that the reaction course is determined by the number of chlorine atoms. 2-and 4-Chloroquinoline-3-carbaldehydes give dihydropyridines and a benzo[c][2,7-]naphthyridine is formed in the reaction with 2,4-dichloroquinoline-3-carbaldehyde. The main products in the case of nitrobenzaldehydes are dihydropyridines which points the deciding influence of the low electrophilicity of aromatic ring.In our recent study of the reaction of α-acylacetamidines (which exist in solution in the tautomeric enediamine form) with 2-fluoro-5-nitrobenzaldehyde (1) and 4,6-dichloro-2-methylsulfanylpyrimidine-5-carbaldehyde (2) the main reaction products are isoquinolines and pyrido[4,3-d]pyrimidines respectively [1,2]. α-Acylacetamidines react as C,N-dinucleophiles. The reaction occurs with a uniform chemo-selectivity: the amidine α-carbon substitutes the halogen atom in the aromatic ring and the amino group binds to the formyl carbon atom. However, in the case of the reaction of ethyl 3,3-diaminoacrylate (3) with the aldehyde 1 the cyclocondensation is accompanied by a concurrent Hantzsch type reaction to form the dihydropyridine 6. This reaction occurs using two molecules of the enediamine and one molecule of the aldehyde. Moreover, only the carbonyl group in the aldehyde reacts, the halogen atom at the aromatic ring being unaffected. In addition, a marked amount of the quinoline 5 is observed in the reaction which, as the dihydropyridine 6, is formed as a result of an attack by the carbon nucleophilic center of the enediamine at the formyl group. At the same time, the reaction of enediamine 3 with compound 2 gives only the corresponding pyrido[4,3-d]pyrimidine in virtually quantitative yield.

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Section: Methodsmentioning

confidence: 99%

“…The reaction of aldehyde 7a with enediamine 3 gave the benzo[c] [2,7]naphthyridine 8a in 77% yield. Its NOESY correlation spectrum showed strong cross peaks between the signal for the methylene in the carbethoxy fragment and the H-10 proton doublet (7.97 ppm).…”

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confidence: 99%

Competitive formation of condensed azines and dihydropyridines in the reaction of ethyl 3,3-diaminoacrylate with o-halo carbaldehydes

Eliseev

Dar’in

Селиванов

et al. 2008

Chem Heterocycl Comp

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“…Hydrolysis of 1 a-c [11,12] with H 2 SO 4 (70 %) gave the 7-substituted quinolin-2(1H)-one-3-carboxylic acids 2 a-c in good yields. Heating 2 a-c in boiling phosphoryl chloride gave the 7-substituted 2-chloroquinoline-3-carboxylic acids 3 a-c.…”

Section: Chemistrymentioning

confidence: 99%

“…This compound was prepared as previously reported [12] starting from 7-methoxy-2-chloroquinoline-3-carboxaldehyde [14], yield (75 %), mp >300°C. …”

Section: -Methoxyquinolin-2(1h)-one-3-carbonitrile 1 Cmentioning

confidence: 99%

Synthesis of Some Novel Quinoline-3-carboxylic Acids and Pyrimidoquinoline Derivatives as Potential Antimicrobial Agents

El-Sayed

Albassam

Hussein

2002

Arch. Pharm. Pharm. Med. Chem.

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“…2-Chloro-3-formylquinoline (1a) and 2-Chloro-3-formyl-7-methylquinoline (1b) were sinthesized as reported in [7], 3-Formylquinol-2-one (2a) and 3-Formyl-7-methylquinol-2-one (2b) as in [8].…”

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confidence: 99%

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Onysko

Lendel

2007

Chem Heterocycl Comp

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There are literature reports of the haloheterocyclization reactions of unsaturated quinoline ethers and thioethers [1] to give heterocyclic systems with oxa(thia)zolinium rings. In continuation of these studies we have selected the 2-allyl(propargyl)oxyquinoline-3-carbaldehydes 3, 4 as model compounds for this haloheterocyclization. These substrates were prepared by conversion of 2-chloro-3-formylquinolines 1 to the corresponding quinolones 2 by treatment with hydrochloric acid and subsequent alkylation using allyl(propargyl) bromides. N R O Cl H 2 O, HCl N R O OH N H R O O N R O O X 2 R O N O X N R O O X 2 R O N O X X X 1a,b 2a,b + 3a,b 5, 6a,b + 4a,b 7, 8a,b KOH KOH CH 2 =CHCH 2 Br HC CCH 2 Br 1 2 3 4 5 6 7 8 -2n+1 -2n+1 1-8 a R = H, b R = Me; 5, 7 Х = Br, n = 0; 6, 8 X = I , n = 1

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A versatile new synthesis of quinolines and related fused pyridines. Part 9. Synthetic application of the 2-chloroquinoline-3-carbaldehydes

Cited by 62 publications

References 0 publications

Competitive formation of condensed azines and dihydropyridines in the reaction of ethyl 3,3-diaminoacrylate with o-halo carbaldehydes

Competitive formation of condensed azines and dihydropyridines in the reaction of ethyl 3,3-diaminoacrylate with o-halo carbaldehydes

Synthesis of Some Novel Quinoline-3-carboxylic Acids and Pyrimidoquinoline Derivatives as Potential Antimicrobial Agents

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

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