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 | |
| 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.