The rearrangement of tosylated flavones to 1 '-(alkylamino)aurones with primary amines
- Author(s)
- Wolfgang Kandioller, Mario Kubanik, Anna K. Bytzek, Michael A. Jakupec, Alexander Roller, Bernhard K. Keppler, Christian G. Hartinger
- Abstract
A rearrangement of 3-tosylflavone to the corresponding 1′-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1′-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed.
- Organisation(s)
- Department of Inorganic Chemistry, Core Facility Crystal Structure Analysis
- External organisation(s)
- University of Auckland
- Journal
- Tetrahedron
- Volume
- 71
- Pages
- 8953-8959
- No. of pages
- 7
- ISSN
- 0040-4020
- DOI
- https://doi.org/10.1016/j.tet.2015.09.062
- Publication date
- 11-2015
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 104015 Organic chemistry
- Keywords
- ASJC Scopus subject areas
- Drug Discovery, Biochemistry, Organic Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/a45091f3-45cc-4dc8-9320-4dddccad0cd7