Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 2, Pages 1955-1963Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02452
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Funding
- National Research Council of Thailand (NRCT) [NRCT5-RSA63002-10]
- Kasetsart University Research and Development Institute (KURDI)
- Science Achievement Scholarship of Thailand (SAST)
- Center of Excellence for Innovation in Chemistry (PERCHCIC), Ministry of Higher Education, Science, Research and Innovation
- Department of Chemistry, and the Faculty of Science, Kasetsart University
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This work describes a novel and simple one-pot synthesis of substituted dibenzo[b,f]oxepines under transition-metal-free conditions, which was achieved through a cascade process involving nucleophilic aromatic substitution followed by Knoevanagel condensation. The synthesis of anticancer bauhinoxepin C was also successfully achieved in 7 steps with 5.1% overall yield using this synthetic approach.
In this work, we report a novel and simple one-pot synthesis of substituted dibenzo[b,f]oxepines under transition-metal-free conditions. This cascade process involves nucleophilic aromatic substitution followed by Knoevanagel condensation, as evidenced by the isolated reaction intermediates. We have also achieved the synthesis of anticancer bauhinoxepin C in 7 steps with 5.1% overall yield using this synthetic approach.
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