Investigations in the region of 2,3′-biquinoline. 3. Synthesis of 2′-alkyl(aryl)-1′,2′-dihydro-2,3′-biquinolines and 2′-alkyl(aryl)-2,3′-biquinolines

Аксенов, А. В.; Nadein, O. N.; Боровлев, И. В.; Smushkevich, Yu. I.

doi:10.1007/bf02290723

Cited by 5 publications

(6 citation statements)

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“…When mixed with a known sample no depression of melting point was produced. The 1 H NMR spectrum was identical to that given in [9]. 2'-Butyl-2,3'-biquinoline (2d).…”

Section: -3'-biquinolyl (2a)mentioning

confidence: 65%

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Investigations on 2,3′-biquinolyl series. 20. Novel method for the synthesis of 2,3′-biquinolines by cyclization of β-(2-quinolyl)-2-aminostyrenes

Lyakhovnenko

Trifonov

Goncharov

et al. 2006

Chem Heterocycl Compd

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A method has been developed for the synthesis of 2,3'-biquinolines based on the reaction of β-(2-quinolyl)-2-aminostyrenes with acid amides under Vilsmeier reaction conditions.A series of methods for the synthesis of 2,3'-biquinolines 2 has been developed which includes either formation of quinoline rings (e.g. in [2-5]) or of a bond between them [6, 7]. These methods have a number of drawbacks which include the low availability of starting compounds or the possibility of synthesizing only symmetrically substituted 2,3'-biquinoline derivatives.In this work we report a method for the synthesis of 2,3'-biquinolines which allows one to synthesize, from one starting compound, 2,3'-biquinolines with different substituents in the 2'-position.We have shown that the reaction of the amines 1a,b with DMF or the diethylamides of other carboxylic acids in the presence of POCl 3 gives high yields (82-88%) of the 2,3'-biquinolines 2a-f. N N R X N N H 2 X 1a,b 2a-f 1) RCONR 1 2 /POCl 3 2) H 2 O 1 a X = H, b X = NO 2 ; 2 a R = H, b R = Me, c R = Pr, d R = Bu, e R = Ph; a-e X = H, f R = H, X = NO 2The reaction of the amine 1 with acid chlorides in the presence of Et 3 N and subsequent treatment with POCl 3 occurs similarly. In this case the yields of the reaction products are lower.

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“…When mixed with a known sample no depression of melting point was produced. The 1 H NMR spectrum was identical to that given in [9]. 2'-Butyl-2,3'-biquinoline (2d).…”

Section: -3'-biquinolyl (2a)mentioning

confidence: 65%

“…B. From benzoyl chloride in 0.52 g (79%) yield; mp 76-77°C (benzenehexane) (mp 76-77°C [9]). When mixed with a known sample no depression of melting point was produced.…”

Section: -3'-biquinolyl (2a)mentioning

confidence: 99%

Investigations on 2,3′-biquinolyl series. 20. Novel method for the synthesis of 2,3′-biquinolines by cyclization of β-(2-quinolyl)-2-aminostyrenes

Lyakhovnenko

Trifonov

Goncharov

et al. 2006

Chem Heterocycl Compd

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“…A melting test with an authentic sample gave no depression of melting point. The 1 H NMR spectrum was identical to that given in [12].…”

Section: Synthesis Of 23'-biquinolines From Anilides Of Quinoline-3-mentioning

confidence: 98%

Investigations in 2,3′-biquinoline series 24. Synthesis of 3-hetarylquinolines and their 1,4-dihydro derivatives under conditions of the Vilsmeier reaction

Glushenko

Goncharov

Аксенов

2008

Chem Heterocycl Comp

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“…In the latter case demethylation and prototropic shift evidently occur. Boiling of benzene solutions of substituted 1,2-dihydroquinolines with MnO 2 leads to their almost quantitative aromatization [81].…”

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confidence: 99%

Oxidation of heterocyclic compounds by manganese dioxide (Review)*

Солдатенков

Polyanskii

Kolyadina

et al. 2009

Chem Heterocycl Comp

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Investigations in the region of 2,3′-biquinoline. 3. Synthesis of 2′-alkyl(aryl)-1′,2′-dihydro-2,3′-biquinolines and 2′-alkyl(aryl)-2,3′-biquinolines

Cited by 5 publications

References 0 publications

Investigations on 2,3′-biquinolyl series. 20. Novel method for the synthesis of 2,3′-biquinolines by cyclization of β-(2-quinolyl)-2-aminostyrenes

Investigations on 2,3′-biquinolyl series. 20. Novel method for the synthesis of 2,3′-biquinolines by cyclization of β-(2-quinolyl)-2-aminostyrenes

Investigations in 2,3′-biquinoline series 24. Synthesis of 3-hetarylquinolines and their 1,4-dihydro derivatives under conditions of the Vilsmeier reaction

Oxidation of heterocyclic compounds by manganese dioxide (Review)*

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