Acid catalysed rearrangement of isobenzofurans to angularly fused phthalides
Bhavani Shankar Chinta1, Soniya Gandhi, Beeraiah Baire
1Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, India. beeru@iitm.ac.in.
Abstract:
An acid catalysed, cascade process for the construction of angularly fused polycyclic phthalides from isobenzofurans under transition metal free conditions has been reported. This process is very general for diverse gem-disubstituted isobenzofuran substrates. Control experiments supported the mechanism as the nucleophilic attack of the carboxylate onto the acid activated furan ring for the simultaneous ring closing-ring opening cascade followed by dehydration. This method serves as a greener alternative for the synthesis of angularly fused polycyclic phthalides.
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