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Synthesis 1993; 1993(1): 107-111
DOI: 10.1055/s-1993-25810
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Heterocyclische ß-Enaminoester; 55.1 Imidazo[4,5-d]-, Thiazolo[5,4-d]- und Thiazolo[4,5-d][1,3]oxazinone

Heinrich Wamhoff* , Rainer Berressem, Stefan Herrmann
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, D-5300 Bonn 1, Germany
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Publication Date:
17 September 2002 (online)

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Heterocyclic ß-Enamino Esters; 55.1 Imidazo[4,5-d]-,Thiazolo[5,4-d]-, and Thiazolo[4,5-d][1,3]oxazinones 5-Aroylamino-, 3a,b, and 5-(3-arylureido)-1-benzyl-1H-imidazole-4-carboxylates 6a,b are converted with dichlorotriphenylphosphorane into 3-benzyl-3,7-dihydro-imidazo[4,5-d][1,3]oxazin-7-ones 4a,b and 7a,b, respectively. Similarly, 5-aroylamino-4-thiazole-carboxylates 10a-f and 4-aroylamino-5-thiazolecarboxylates 14a-d are cyclized with dibromotriphenylphosphorane (11) to afford thiazolo[5,4-d]-, 12a-f, and thiazolo[4,5-d][1,3]oxazin-7-ones 15a-d, respectively.