a one-step synthesis of pyrazolone一步法合成的吡唑啉酮.pdfVIP

Molbank 2004 Molbank 2006, M464 /molbank/ A onestep synthesis of pyrazolone Gernot A. Eller* and Wolfgang Holzer Department of Drug Synthesis, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria Phone: +431427755634, email: gernot.eller@univie.ac.at *Author to whom correspondence should be addressed Received: 3 January 2006 / Accepted: 4 January 2006 / Published: 22 January 2006 Keywords: Pyrazolone, cyclization, NMR spectroscopy, tautomerism. Abstract : The fully unsubstituted pyrazolone (= 2pyrazolin5one, which is tautomer to 1 pyrazol3ol and 1 pyrazol5ol) was prepared from hydrazine hydrate and methyl (2E)3 1 13 15 methoxyacrylate in almost quantitative yield. Detailed spectroscopic data ( H NMR, C NMR, N NMR, MS) for this compound are presented. Substituted 2pyrazolin5ones play an important role as substructures of numerous pharmaceuticals, agrochemicals, dyes, pigments, as well as chelating agents and thus attract remarkable attention [1,2]. Recently, we investigated the synthesis of some N1unsubstituted pyrazolones by use of the PMB (p methoxybenzyl) protecting group [3,4]. Although this substituent proved to be conveniently removable from various 4substituted pyrazolones upon treatment with refluxing trifluoroacetic acid only poor results were obtained when the parent 1PMBpyrazolone (= 2(4methoxybenzyl)2,4dihydro 3 pyrazol3one [3]) was