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Paper | Regular issue | Vol 51, No. 3, 1999, pp.513-546
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8385
Syntheses of Phosphonato-substituted Azolo[1,2,4]triazines with Potential Biomedical Applications

Thomas Ankenbrand and Richard Neidlein*

*Pharmazeutisch-Chemishces Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 364, D-69120 Heidelberg, Germany

Abstract

The syntheses of [1,2,4]triazino[4,3-b][1,2,4]indazol-3-yl-phosphonic acid dialkyl esters (5-7), pyrazolo[3,2-c][1,2,4]triazin-3-yl-phosphonic acid dialkyl esters (9-11) and [1,2,4]triazolo[3,2-c][1,2,4]triazin-3-ylphosphonic acid dialkyl esters (13-15) are desribed. The treatment of 7-methylpyrazolo[1,2,4]triazin derivatives (9c,d, 11c-e) with N-bromo- or N-iodosuccinimide yields the corresponding 8-halogen compounds (19a-h). The 8-iodo derivatives could be coupled with phenylacetylene.