Issue 32, 2016
From the journal:

Chemical Communications

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,a   Jopaul Mathewa  and  S. S. V. Ramasastry*a  

* Corresponding authors

a Organic Synthesis and Catalysis Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, S. A. S. Nagar, Manuali PO, Punjab 140306, India
E-mail: ramsastry@iisermohali.ac.in, ramsastrys@gmail.com
Web: http://14.139.227.202/faculty/sastry/

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.

Graphical abstract: 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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Article information

DOI
https://doi.org/10.1039/C6CC01016D
Article type
Communication
Submitted
01 Feb 2016
Accepted
17 Mar 2016
First published
17 Mar 2016
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2016,52, 5569-5572

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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

S. K. Bankar, J. Mathew and S. S. V. Ramasastry, Chem. Commun., 2016, 52, 5569 DOI: 10.1039/C6CC01016D

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