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Synlett 2025; 36(01): 59-64
DOI: 10.1055/a-2312-0444
DOI: 10.1055/a-2312-0444
letter
Unexpected One-Pot Synthesis of 3-Cinnamoyl-3-hydroxyphthalide Derivatives
The authors would like to thank the National Research Council of Thailand (NRCT: NRCT5-RSA63002-10), the Graduate School, Kasetsart University (through the Graduate School Fellowship Program), the Kasetsart University Research and Development Institute (KURDI), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, the Thailand Toray Science Foundation (TTSF), and the Department of Chemistry and Faculty of Science, Kasetsart University, for financial support.
Abstract
A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 °C with K3PO4 as a base and AlCl3 as a catalyst. We propose that the reaction proceeds by a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structure of the hydroxyphthalide derivatives.
Key words
hydroxyphthalides - one-pot synthesis - cascade reaction - natural product - benzaldehydesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2312-0444.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. März 2024
Angenommen nach Revision: 23. April 2024
Accepted Manuscript online:
23. April 2024
Artikel online veröffentlicht:
03. Mai 2024
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References and Notes
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