New method for synthesis of 7-hydroxydibenzopyran-6-ones: Benzannulation of coumarins by three-component condensation

We have achieved a simple, facile and three-component synthesis of C8 and C9 alkyl/aryl C7-hydroxydibenzopyrans-6-ones involving C3-acyl coumarins, selective active methylene compounds and some methyl ketones (reagent/solvent) under basic (K2CO3) conditions. Overall, our method worked by benzannulat...

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Bibliographic Details
Published in:Tetrahedron 2023-02, Vol.132, p.133234, Article 133234
Main Authors: Surya Prakash Rao, H., Prabakaran, M., Muthanna, Nandurka
Format: Article
Language:English
Subjects:
Benzannulation
Coumarin
Dibenzopyran-6-one
Murayalactone analogues
Photolytic deprotection
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Summary:We have achieved a simple, facile and three-component synthesis of C8 and C9 alkyl/aryl C7-hydroxydibenzopyrans-6-ones involving C3-acyl coumarins, selective active methylene compounds and some methyl ketones (reagent/solvent) under basic (K2CO3) conditions. Overall, our method worked by benzannulation of the existing coumarins. In this work, we used the 2-NB group (2-NB = 2-nitrobenzyl) as a surrogate for C7–OH to engineer the construction of the ring C of the 3-hydroxydibenzopyran-6-ones. Subsequently, the photolabile 2-NB was removed under neutral conditions to reveal the C3–OH. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.133234