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Synthesis 2000; 2000(14): 2009-2012
DOI: 10.1055/s-2000-8721
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3,9-Dihydro-2H-[1,2,4]-oxadiazolo[3,2-b]quinazolin-2-ones: First Synthesis of the Parent Heterocycle, 7- and 9-Substituted Derivatives

Patrice P. Renaut* , Philippe Durand, Philippe Ratel
  • *Laboratoires Fournier, S.A., 50 rue de Dijon, 21121 Daix, France; Fax +33(3)80 44 75 38; E-mail: p.renaut@fournier.fr
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Publication Date:
31 December 2000 (online)

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A first synthesis of 3,9-dihydro-9-aryl-2H-[1,2,4]-oxadiazolo[3,2-b]quinazolin-2-ones is described via the thermal cyclisation of ethyl-(4-aryl-3-oxido-2-quinazolinyl)-carbamates followed by borohydride reduction. A more direct route to 3,9-dihydro-2H-[1,2,4]-oxadiazolo[3,2-b]quinazolin-2-ones, involving the reductive-ring closure of ethyl-(3-oxido-2-quinazolinyl)-carbamate, gives access to the parent unsubstituted heterocycle in good yield. This reaction has been extended to a variety of 7- and 9-substituted 3,9-dihydro-2H-[1,2,4]-oxadiazolo[3,2-b]quinazolin-2-ones.

[1,2,4]oxadiazolo[3,2-b]quinazolin-2-one - thermal cyclisation - borohydride reduction - reductive-ring closure

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