Publication

2-(Trifluoromethyl)quinolines from anilines: a novel mode of isomerization and cyclization

Manfred Schlosser
1996
Journal Articles

Abstract

Deprotonation of N-ethylidene-tert-butylamine with lithium diisopropylamide and subsequent condensation with Et trifluoroacetate gives 4-tert-butylamino-1,1,1-trifluorobut-3-en-2-one. An exchange of the amino substituent occurs when the latter compd. is treated with anilines under mildly acidic conditions. When heated in the presence of phosphoryl trichloride, the resulting 4-anilino-1,1,1-trifluorobut-3-en-2-ones undergo an N -> ortho shift of the side chain followed by cyclization and dehydration to afford 2-(trifluoromethyl)quinolines. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/d6480438-3356-4ad7-aad7-f45e2a3e5d9e

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Manfred Schlosser
1996
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d6480438-3356-4ad7-aad7-f45e2a3e5d9e

About this result

Related concepts (9)

Amino acid

Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the α-amino acids, from which proteins are composed. Only 22 α-amino acids appear in the genetic code of all life. Amino acids can be classified according to the locations of the core structural functional groups, as alpha- (α-), beta- (β-), gamma- (γ-) or delta- (δ-) amino acids; other categories relate to polarity, ionization, and side chain group type (aliphatic, acyclic, aromatic, containing hydroxyl or sulfur, etc.

Non-proteinogenic amino acids

In biochemistry, non-coded or non-proteinogenic amino acids are distinct from the 22 proteinogenic amino acids (21 in eukaryotes) which are naturally encoded in the genome of organisms for the assembly of proteins. However, over 140 non-proteinogenic amino acids occur naturally in proteins and thousands more may occur in nature or be synthesized in the laboratory. Chemically synthesized amino acids can be called unnatural amino acids.

Side chain

In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition.