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New Benzo[b]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho-Benzoquinodimethanes

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Summary.

 New benzo[b]xanthone derivatives, having substituents in the A and D rings, were prepared from cycloaddition reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethanes, generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, followed by oxidation of the obtained diastereomeric adducts. The structure of all compounds was fully established by 1D and 2D NMR, MS, and elemental analysis. The stereochemistry of the obtained diastereomeric cycloadducts was established by NOESY experiments.

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Authors and Affiliations

  1. Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, , , , , , PT

    Angela Sandulache, Artur M. S. Silva & José A. S. Cavaleiro

Authors
  1. Angela Sandulache
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  2. Artur M. S. Silva
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  3. José A. S. Cavaleiro
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Corresponding author. E-mail: arturs@dq.ua.pt

Received September 16, 2002; accepted September 20, 2002

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Sandulache, A., Silva, A. & Cavaleiro, J. New Benzo[b]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho-Benzoquinodimethanes. Monatshefte für Chemie 134, 551–563 (2003). https://doi.org/10.1007/s00706-002-0567-7

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  • DOI: https://doi.org/10.1007/s00706-002-0567-7

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