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Synthesis 1991; 1991(8): 625-628
DOI: 10.1055/s-1991-26529
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New [f]-Fused Theophyllines via Intramolecular Nucleophilic Addition of Alkyl (E)-4-[(8-Substituted)theophyllin-7-yl]-2-butenoate

Dušan Hesek* , Alfonz Rybár, Juraj Bella
  • *Drug Research Institute, CS-900 01 Modra, Czechoslovakia
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Publication Date:
29 April 2002 (online)

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A simple synthetic route to [f]-annulated theophyllines ([f]-annulated 3,7-dihydro-1,3-dimethyl-1H-purine-2,6-diones) is described, based on intramolecular nucleophilic addition, and starting from ethyl (E)-4-[(8-substituted) theophyllin-7-yl]-2-butenoates. The presence of an 8-hydroxymethyl group enables the formation of hexahydro-9H-[1,4]oxazino[3,4-f]purine derivatives 3a, in the case of an 8-methylthio substituent, 8, the products are hexahydro- 9H-[1,4]thiazino[3,4-f]purine 9, and similarly with 8-hydrazino derivatives 12, octahydro[1,2,4]triazino[3,4-f]purines 14 are obtained.