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Synlett 1997; 1997(9): 1105-1107
DOI: 10.1055/s-1997-1536
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2,4-Dimethoxy-1,3-diazaanthracene, a Diels-Alder Diene for the Preparation of Polyalicyclic Structures Functionalised with Uracil Subunits

Ronald N. Warrener* , Mirta Golic, Douglas N. Butler
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia, Fax: +61 79 30 9917; email: r.warrener@cqu.edu.au
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Publication Date:
31 December 2000 (online)

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2,4-Dimethoxy-1,3-diazaanthracene (DDA) has been prepared from the known 2,4-dichloro-1,3-diazaanthracene by methoxide displacement of the chloro-substituents and shown to react as a diene in Diels-Alder reactions with electron-deficient and ring-strained dienophiles. Sodium hydroxide fusion is used to transform the DDA adducts to uracil derivatives.

cycloaddition - pyrimidine - NaOH fusion - site and stereoselectivity