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- Title
Reaction of nitroanilines with aldehydes. Refinement of the Doebner-Miller reaction mechanism.
- Authors
Denisov, V.; Grishchenkova, T.; Tkachenko, T.; Luzgarev, S.
- Abstract
Due to intramolecular hydrogen bonding between the amino and nitro groups, o-nitroaniline is incapable of forming Schiff bases in the reactions with acetaldehyde and crotonaldehyde but is converted to quinoline derivative under Doebner-Miller reaction conditions via addition to the C=C double bond of the α,β-unsaturated aldehyde. Under analogous conditions, p-nitroaniline possessing a free amino group gives rise to the product of Doebner-Miller quinoline synthesis through intermediate formation of Schiff base dimer. The reaction of p-nitroaniline with benzaldehyde also yields the corresponding Schiff base, whereas o-nitroaniline is converted to N-benzyl derivative.
- Subjects
CHEMICAL reactions; NITROANILINE; ALDEHYDES; HYDROGEN bonding; SCHIFF bases; AMINO group
- Publication
Russian Journal of Organic Chemistry, 2016, Vol 52, Issue 12, p1797
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428016120150