Abstract |
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 H-1, P-31, and C-13 NMR and IR spectroscopies and mass spectrometry. The molecular structure of compound 6 was confirmed by X-ray diffraction studies. C (C) 2015 Wiley Periodicals, Inc. |