Issue 17, 2012

Chemistry of 9,10-phenanthrenequinone revisited: iron(iii) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

Abstract

9,10-Phenanthrenequinone (PQ) reacts with ketones under FeCl3 catalysis to furnish a variety of structurally diverse furan annulated products. While the reaction of PQ with acetone and cyclopentanone furnishes furan annulated ketals, its reaction with ethyl alkyl ketones provides 3-furaldehyde annulated products. In contrast to the reaction of PQ with cyclopentanone, its reaction with cyclohexanone furnishes a tetrahydrobenzofuran annulated secondary alcohol. The reactions of PQ with cycloheptanone and cyclooctanone take a different course to provide 7,8-dihydro-6H-cyclohepta[b]furan and 6,7,8,9-tetrahydrocycloocta[b]furan annulated products, respectively. Mechanistically, the above reactions go through aldol condensation, dehydration and cyclization to form furan-phenanthrene annulated products where in each step FeCl3 catalysis is involved.

Graphical abstract: Chemistry of 9,10-phenanthrenequinone revisited: iron(iii) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2012
Accepted
26 May 2012
First published
28 May 2012

RSC Adv., 2012,2, 6773-6783

Chemistry of 9,10-phenanthrenequinone revisited: iron(III) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

H. Surya Prakash Rao and S. Vijjapu, RSC Adv., 2012, 2, 6773 DOI: 10.1039/C2RA20499A

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