Reactions with 1(2H)-phthalazinones, 4,5-dihydro-3(2H)-pyridazinones and 3-pyrazolin-5-ones |
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| Affiliation: | 1. Laboratório de Pesquisas em Virologia, Departamento de Doenças Dermatológicas, Infecciosas e Parasitarias, Faculdade de Medicina de São José do Rio Preto − FAMERP, 15090-000, São José do Rio Preto, SP, Brazil;2. Faceres Medical School, 15090-305, São José do Rio Preto, SP, Brazil;3. Laboratório de Imunofarmacologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, 31270-901, Belo Horizonte, MG, Brazil;4. Departamento de Ciências Farmacêuticas, Centro de Ciências da Saúde, Universidade Federal de Pernambuco, 50740-521, Recife, PE, Brazil;1. Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060–0812, Japan;2. Center for Pharma-Food Research (CPFR), Graduate School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422–8526, Japan;1. Interdisciplinary Research Department—Field Science, ‘Alexandru Ioan Cuza’ University, Lascar Catargi Str. 54, 700107 Iasi, Romania;2. Laboratory of organic synthesis, Institute of Chemistry, Academy of Sciences of Moldova, Academy Str. 3, MD-2028 Chisinau, Republic of Moldova;3. BAM Federal Institute for Materials Research and Testing, Unter den Eichen 87, 12205 Berlin, Germany;4. National Institute of Research and Development for Technical Physics, Dimitrie Mangeron Bd. 47, 700050 Iasi, Romania;5. Humboldt-Universität zu Berlin, Department of Chemistry, Brook-Taylor-Str. 2, 12489 Berlin, Germany;1. Romanian Academy “Coriolan Dragulescu” Institute of Chemistry, 24 Mihai Viteazul Ave, Timisoara 300223, Romania;2. Department of Chemical Engineering, Faculty of Engineering, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece;3. Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece;1. PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany;2. KU Leuven, Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Minderbroedersstraat 10, 3000 Leuven, Belgium |
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| Abstract: | The condensation of 1(2H)-phthalazinones (Ia-c), 4,5-dihydro-6-phenyl-3(2H)-pyridazinone (IIIa), and 4-arylidene-4,5-dihydro-6-phenylpyridazinones (IVa-b) with secondary amines and formaldehyde yields the corresponding N-Mannich-bases (Id, IIIc-d, and IVi-j, respectively). Similarly, reaction with acrylonitrile, affords the cyanoethylated products (Ig, IIIf, and IVk-1, respectively). The Mannich-bases (Id) are also obtained by reaction of the appropriate amines with the corresponding chloromethyl- (If), or hydroxymethylphthalazinone derivatives (Ie); and by treatment of the hydroxymethyl derivative of IIIa with the same reagents. In the presence of ethyl-amine, the condensation of la-c with formaldehyde yields the corresponding bis-derivatives (II).The reaction of 3-methyl-2-phenyl-3-pyrazolin-5-one (Va) with formaldehyde and piperidine or morpholine involves the hydrogen atom on C4 with formation of the Mannich-bases (Vd-e). In addition, the synthesis of some of the corresponding bis-derivati es (VI) are reported. The IR spectra of the reaction products are discussed. Interaction of Vd with aromatic thiols leads to the formation of 4-arylthiomethyl-3-methyl-2-phenyl-3-pyrozolin-5-ones (IVf-i). The latter compounds react with ethereal diazomethane yielding products believed to have structures similar to VII.Treatment of 2-N-piperidinomethyl-4-phenyl-1(2H)-phthalazinone (cf. Id), and 2-N-piperidino-methyl-6-phenyl-4,5-dihydro-3(2H)-pyridazinone (IIIe) with phenylmagnesium bromide, followed by hydrolysis, gives 1,4-diphenylphthalazine and 3,6-diphenylpyridazine (VIII), respectively. The latter has also been obtained by the action of the same reagent on IIIa and/or 6-phenyl-3(2H)-pyridazinone. |
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