Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones

Siddheshwar K. Bankar; Jopaul Mathew; S. S.V. Ramasastry

doi:10.1039/c6cc01016d

Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones

Siddheshwar K. Bankar, Jopaul Mathew, S. S.V. Ramasastry

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26 Scopus citations

Abstract

An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-β-pyrones and phenols is presented. The synthetic sequence involves a cascade transacetalisation, Fries-type O → C rearrangement followed by Michael addition and ring-opening aromatisation. The versatility of this method was further demonstrated via the synthesis of 4,4a-dihydropyrano[3,2-b]benzofuran-3-ones, furo[3,2-c]coumarins, and spiro[benzofuran-2,2′-furan]-4′-ones. The unexpected cascade event would also provide new possible considerations in the β-pyrone-involved organic synthesis.

Original language	English
Pages (from-to)	5569-5572
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	32
DOIs	https://doi.org/10.1039/c6cc01016d
State	Published - Apr 25 2016
Externally published	Yes

Funding

We thank the DST (SR/FT/CS-156/2011) and IISER Mohali for funding. We also thank NMR, mass, and departmental X-ray facilities at IISER Mohali. S. K. B. thanks IISER Mohali for a research fellowship and J. M. thanks DST, Govt. of India, for the INSPIRE fellowship.

Funders	Funder number
Department of Science and Technology, Ministry of Science and Technology, India	SR/FT/CS-156/2011
Indian Institute of Science Education and Research Mohali

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abstract = "An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-β-pyrones and phenols is presented. The synthetic sequence involves a cascade transacetalisation, Fries-type O → C rearrangement followed by Michael addition and ring-opening aromatisation. The versatility of this method was further demonstrated via the synthesis of 4,4a-dihydropyrano[3,2-b]benzofuran-3-ones, furo[3,2-c]coumarins, and spiro[benzofuran-2,2′-furan]-4′-ones. The unexpected cascade event would also provide new possible considerations in the β-pyrone-involved organic synthesis.",

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AB - An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-β-pyrones and phenols is presented. The synthetic sequence involves a cascade transacetalisation, Fries-type O → C rearrangement followed by Michael addition and ring-opening aromatisation. The versatility of this method was further demonstrated via the synthesis of 4,4a-dihydropyrano[3,2-b]benzofuran-3-ones, furo[3,2-c]coumarins, and spiro[benzofuran-2,2′-furan]-4′-ones. The unexpected cascade event would also provide new possible considerations in the β-pyrone-involved organic synthesis.

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Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones

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