Untitled

Аксенов, А. В.; Demidova, N. V.

doi:10.1023/a:1020961211554

Cited by 5 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is likely that the reaction involves the formation of dihydro derivatives of 2,3'-biquinoline. A similar conclusion can be reached from the fact that the regioselectivity of the reaction is similar to the halogenation of the dihydro derivatives [6].…”

Section: _______supporting

confidence: 67%

See 1 more Smart Citation

Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives

Demidova

Karaivanov

Goncharov

et al. 2005

Chem Heterocycl Compd

Self Cite

View full text Add to dashboard Cite

It is known that the halogenation of quinoline in strongly acidic medium occurs at position 5 and 8 forming a 1:1 ratio of isomers. It is thought that such an orientation is a consequence of the deactivation of the pyridine ring due to protonation [2,3].In the case of less strong acid the quinoline is initially substituted at position 3 and then at position 6 and 8 and this arises from its initial conversion to the quinolinium cation which reacts with a nucleophile at position 2 to form a 1,2-dihydroquinoline. Subsequent addition of the electrophile occurs at position 3 etc [2, 3].2,3'-Biquinoline was of interest as a model compound for the investigation of electrophilic substitution in quinolines because, as a result of its asymmetry, a monoprotonation principally at one of the nitrogen atoms might be expected. In this case the reaction of a first kind would occur on a nonprotonated quinoline fragment and permit an evaluation of the regioselectivity of the electrophilic substitution in the quinoline free base and in the second kind on the other ring.We have previously shown [4] that the 2,3'-biquinoline 1 is nitrated by potassium nitrate in sulphuric acid on the 2-quinoline fragment and this agrees with a direction of monoprotonation of 2,3'-biquinoline at the nitrogen atom in position 1'. With the above in mind the halogenation of 2,3'-biquinoline in the presence of acid would be expected to occur in the 2-quinoline fragment at positions 5 and 8. In fact, treatment of compound 1 with bromine or chlorine in sulphuric acid in the presence of Ag 2 SO 4 gives a mixture of the 8-halo-2,3'-biquinoline 2, the 5-halo-2,3'-biquinoline 3, and the 5,8-dihalo-2,3'-biquinoline 4 in the ratio 2:1:4 (from 1 H NMR spectroscopic data).

show abstract

Section: _______supporting

confidence: 67%

“…In a study of the halogenation of the dihydro derivatives of 2,3'-biquinoline it was found that they readily undergo oxidation [6].…”

Section: _______mentioning

confidence: 99%

Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives

Demidova

Karaivanov

Goncharov

et al. 2005

Chem Heterocycl Compd

Self Cite

View full text Add to dashboard Cite

show abstract

“…A mixing test with an authentic sample gave no depression of melting point. The 1 H NMR spectrum was identical to that given in [13]. Lit.…”

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

confidence: 55%

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

Self Cite

View full text Add to dashboard Cite

Investigations in the Field of 2,3′‐Biquinolyl. Part 14. Reaction of Dihydro Derivatives of 2,3′‐Biquinolyl with Bromine and Iodine.

Аксенов

Demidova

2003

ChemInform

View full text Add to dashboard Cite

show abstract

Untitled

Cited by 5 publications

References 0 publications

Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives

Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives

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

Investigations in the Field of 2,3′‐Biquinolyl. Part 14. Reaction of Dihydro Derivatives of 2,3′‐Biquinolyl with Bromine and Iodine.

Contact Info

Product

Resources

About