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Synlett
DOI: 10.1055/a-2312-0444
letter

Unexpected One-Pot Synthesis of 3-Cinnamoyl-3-hydroxyphthalide Derivatives

Intouch Rakchaya
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
,
Phanida Thongaram
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
,
Sengchan Saiyalard
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
,
Kredmanee Yimnoi
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
,
Worawat Wattanathana
b   Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Bangkok 10900, Thailand
,
Nutthawat Chuanopparat 
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
,
Paiboon Ngernmeesri  ∗
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
› Author AffiliationsThe 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.
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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 - benzaldehydes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2312-0444.
  • Supporting Information


Publication History

Received: 04 March 2024

Accepted after revision: 23 April 2024

Accepted Manuscript online:
23 April 2024

Article published online:
03 May 2024

© 2024. Thieme. All rights reserved

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