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Novel Bisphosphonates Derived From 1H‐Indazole, 1H‐Pyrazolo[3,4‐b]Pyridine, And 1H‐Pyrazolo[3,4‐b]Quinoline

Fátima C. Teixeira, Carla Lucas, M. Curto, A. S. Teixeira, M. Duarte, V. André
Published 2016 · Chemistry

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Novel tetraethyl ethylene-1,1-bisphosphonate esters derived from 1H-indazole, 1H-pyrazolo[3,4-b]pyridine, and 1H-pyrazolo[3,4-b]quinoline were synthesized by a Michael addition reaction of tetraethyl ethylidene-1,1-bisphosphonate with the corresponding heterocycle, using conventional heating and microwave-assisted methods. The microwave-assisted method provides shorter reaction times and better yields. The hydrolysis of bisphosphonates afforded the corresponding bisphosphonic acids or salt, using concentrated hydrochloric acid or TMSBr/collidine, respectively. All new compounds were fully characterized, and their structures were assigned using 1H, 31P, and 13C NMR and IR spectroscopies and mass spectrometry. The molecular structure of compound 6 was confirmed by X-ray diffraction studies.
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