Enantioselective Assembly of Tricyclic Tetrahydroquinoline Derivatives

Mustafa Z. Kazancioglu, Erbay Kalay, Elif Akin Kazancioglu, Vsevolod A. Peshkov

Research output: Contribution to journalArticle

Abstract

A three-step synthetic route towards enantioenriched tricyclic tetrahydroquinoline derivatives has been investigated. The first step involved the assembly of 4-amino-tetrahydroquinoline core through the asymmetric three-component Povarov reaction of benzyl (E)-prop-1-en-1-ylcarbamate and p-anisidine with aliphatic aldehydes of various length bearing protected hydroxyl group. The alcohol was then deprotected and employed in an intramolecular reaction with a secondary amine of tetrahydroquinoline moiety producing desired tricyclic scaffolds.

Original languageEnglish
Pages (from-to)8797-8799
Number of pages3
JournalChemistrySelect
Volume4
Issue number30
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Derivatives
Bearings (structural)
Aldehydes
Scaffolds
Hydroxyl Radical
Amines
Alcohols
1,2,3,4-tetrahydroquinoline
4-anisidine

Keywords

  • Asymmetric synthesis
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Povarov reaction
  • Tetrahydroquinolines

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantioselective Assembly of Tricyclic Tetrahydroquinoline Derivatives. / Kazancioglu, Mustafa Z.; Kalay, Erbay; Kazancioglu, Elif Akin; Peshkov, Vsevolod A.

In: ChemistrySelect, Vol. 4, No. 30, 01.01.2019, p. 8797-8799.

Research output: Contribution to journalArticle

Kazancioglu, Mustafa Z. ; Kalay, Erbay ; Kazancioglu, Elif Akin ; Peshkov, Vsevolod A. / Enantioselective Assembly of Tricyclic Tetrahydroquinoline Derivatives. In: ChemistrySelect. 2019 ; Vol. 4, No. 30. pp. 8797-8799.
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