Stereodefined ring contraction-rearrangement of thiocoumarins to new fused benzo[b]thiophene derivatives |
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| Authors: | Massimiliano CordaroGiovanni Grassi Antonio RescifinaUgo Chiacchio Francesco RisitanoAngela Scala |
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| Institution: | a Dipartimento di Chimica Organica e Biologica, Università, Vill. S. Agata, I-98166 Messina, Italyb Dipartimento di Scienze Chimiche, Università di Catania, I-95125 Catania, Italy |
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| Abstract: | Mesoionic 1,3-oxazolium-5-olates (münchnones) react with thiocoumarins having an electron-withdrawing group at the 3-position to afford stereodefined fused polycyclic thienopyrroles. The reaction sequence seems to be triggered by a regiospecific dipolar cycloaddition followed by ring opening of the initial 1:1 cycloadduct and intramolecular rearrangement with an unusual ring contraction. |
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| Keywords: | 1 3-Oxazolium-5-oxides 1 3-Cycloaddition Stereoselectivity Domino reaction |
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