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Synthese stereospecifique de cis-pyrethroides par voie cyclopropenique utilisant un synthon carbanionique : II. Acces aux derives cis-chrysanthemiques et cis-pyrethriques
Affiliation:1. University of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac, Serbia;2. University of Belgrade-Faculty of Chemistry, Studentski trg 16, 11158 Belgrade, Serbia;3. Anorganisch-Chemisches Institut, University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;4. Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Serbia;5. Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, 11000 Belgrade, Serbia;6. Serbian Academy of Sciences and Arts, Knez Mihailova 35, 11000 Belgrade, Serbia;1. Laboratorio de Química Farmacéutica, Facultad de Química, Universidad de la República, Montevideo, Uruguay;2. Instituto de Biología Molecular y Celular de Rosario (IBR-CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Rosario, Argentina;3. Laboratorio de Cristalografía, Química del Estado Sólido y Materiales, Cátedra de Física, DETEMA, Facultad de Química, Universidad de la República, Montevideo, Uruguay;1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic;2. Department of Biological and Biochemical Sciences, Faculty of Chemical Technology, University of Pardubice, Studentska 573, Pardubice 532 10, Czech Republic;3. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic;4. Institute of Organic Chemistry and Biochemistry v.v.i and Gilead Sciences and IOCB Research Center, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 166 10 Prague 6, Czech Republic;5. Regional Center of Advanced Technologies and Materials, Department of Physical Chemistry, Palacký University, Olomouc, 771 46 Olomouc, Czech Republic;1. International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan;2. Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan;3. Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
Abstract:The photolysis of a series of gem-dimethyl 4-carbomethoxy 3H-pyrazoles, obtained from a ummon carbanionic precursor (preceding articals) leads to Cyclopropenic esters.These can be hydrogenated to the corresponding cis-disubstituted cyclopropanes which are direct precursors of chrysanthemates, pyrethric esters and analogous halopyrethroids.
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