Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 39, Pages 8544-8553Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01151k
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Funding
- Department of Atomic Energy
- Science and Engineering Research Board (SERB), New Delhi [EMR/2017/005521]
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Functionalised 4-amino-2-(methylthio)quinolines were successfully synthesised through triflic acid-mediated N-heteroannulation, demonstrating high chemoselectivity and mild reaction conditions. Additionally, a new double N-heteroannulation process was developed for the synthesis of complex indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine was efficiently synthesised in four steps from an acyclic precursor.
Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of alpha-functionalized-beta-anilino-beta-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the beta-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.
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