Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 19, Pages 11552-11570Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01520
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Funding
- CSIR [MLP0203/HCP0010]
- Science and Engineering Research Board, India [EMR/2014/001023]
- UGC, New Delhi
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A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cyclo-additions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N'-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.
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