Mesoionic 1,3-oxazolium-5-olates (manchnones) 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. (C) 2010 Elsevier Ltd. All rights reserved.

Stereodefined ring contraction-rearrangement of thiocoumarins to new fused benzo[b]thiophene derivatives

RESCIFINA, Antonio;CHIACCHIO, Ugo;
2011-01-01

Abstract

Mesoionic 1,3-oxazolium-5-olates (manchnones) 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. (C) 2010 Elsevier Ltd. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/44077
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