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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1603-1613
Published online, 12th November, 2013
DOI: 10.3987/COM-13-S(S)112
Introducing the Diels-Alder Reactivity of 2-Furanmethanethiol with Selected Maleic Acid Derivatives

Mohanad Gh. Shkoor, Irena Nikoloska, and Adrian L. Schwan*

*Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada


Surprising chemoselectivity is demonstrated in the reaction of 2-furanmethanethiol with maleic anhydride and with N-phenylmaleimide. These maleic acid derivatives demonstrate a predilection for Diels-Alder cycloaddition, forgoing both conjugate addition and initial carbonyl attack. N-Ethylmaleimide showed a preference for conjugate addition, whereas diethyl fumarate or dimethyl maleate proved unreactive. The cycloadduct of 2-furanmethanethiol and maleic anhydride was subjected to dehydration/aromatization conditions to create benzo[c]thiophen-1(3H)-one-7-carboxylic acid. An alkylation attempt also led to the formation of a thiolester.