Reaktionen mit cyclischen Oxalylverbindungen,XXIV. Zur Reaktion von 4-Benzoyl-5-phenyl-furan-2,3-dion mit Phenylhydrazonen bzw. Phenylhydrazin |
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| Authors: | Yunus Akcamur Gerhard Penn Erich Ziegler Heinz Sterk Gert Kollenz Karl Peters Eva-Maria Peters Hans Georg von Schnering |
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| Institution: | (1) Organic Kimya Bölümü, Istanbul Universitesi, Mühendislik Fakültesi, Istanbul, Türkei;(2) Institut für Organische Chemie, Universität Graz, A-8010 Graz, Österreich;(3) Max-Planck-Institut für Festkörperforschung, D-7000 Stuttgart 80, Bundesrepublik Deutschland |
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| Abstract: | 4-Benzoyl-5-phenyl-furan-2,3-dione (1) reacts with various phenylhydrazones2 at 60–80°C to the pyrazole carboxylic acid3 a, which then can be decarboxylated to 4-benzoyl-1,5-diphenyl-pyrazole (5).1 and phenylhydrazine combine again yielding3 a as the main product and the isomeric pyridazinone6 as by-product. At higher temperatures (120–140°C) the reaction of1 with2 a leads to the formation of dibenzoyl acetic acid hydrazide derivatives8.The structures of all products were confirmed by IR, MS,15N- and13C-NMR spectroscopic measurements, in the case of the pyridazinone6 also by an X-ray study.6 crystallizes with one moleDMSO monoclinically in space group P 21/n (Nr. 14) with 4 molecules6 andDMSO per cell.The reaction pathways leading to the compounds3, 6 and8 are discussed. |
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| Keywords: | 4-Benzoyl-1 5-diphenyl-pyrazol-3-carboxylic acid 5-Benzoyl-2 6-diphenyl-4-hydroxy-pyridazin-3-one X-Ray structure analysis 15N and13C-NMR spectroscopy |
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