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CC BY-ND-NC 4.0 · Synthesis 2017; 49(23): 5238-5250
DOI: 10.1055/s-0036-1590931
DOI: 10.1055/s-0036-1590931
paper
Synthesis of Chiral Thiourea-Thioxanthone Hybrids
Financial support by the European Research Council under the European Union’s Horizon 2020 research and innovation programme (grant agreement No 665951 – ELICOS) and the Alexander von Humboldt-Stiftung (postdoctoral fellowship to E. R.) is gratefully acknowledged.Further Information
Publication History
Received: 10 August 2017
Accepted: 12 September 2017
Publication Date:
19 October 2017 (online)
Abstract
Four different 1-aminocyclohexanes bearing a tethered thioxanthone group in the 2-position were prepared. The synthesis commenced with the respective N-protected β-amino acids, the carboxyl group of which was employed for the introduction of the thioxanthone moiety. After construction of the thioxanthone and protecting group removal, the conversion of the amino group into the respective thiourea was accomplished by treatment with N-3,5-bis(trifluoromethyl)phenyl isothiocyanate and yielded the title compounds in which the thioxanthone resides in different spatial positions relative to the thiourea motif. Overall yields varied between 20–35%.
Key words
amino acids - chiral pool - esterification - indium - oxazoles - photochemistry - thiourea - thioxanthoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590931.
- Supporting Information
Primary Data
- for this article are available online at https://doi.org/10.1055/s-0036-1590931 and can be cited using the following DOI: 10.4125/pd0096th.
- Primary Data
-
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