5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines |
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Authors: | Mauro Panunzio Emiliano Tamanini Elisa Bandini Eileen Campana Antonio D'Aurizio Paola Vicennati |
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Institution: | aI.S.O.F-C.N.R. Department of Chemistry, University of Bologna, ‘G. Ciamician’ Via Selmi 2, 40126 Bologna, Italy bI.S.O.F-C.N.R. Via Gobetti 101, 40122 Bologna, Italy |
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Abstract: | The synthesis of 5-phenylthio-1,3-oxazinan-4-ones, through a hetero Diels–Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1,3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported. |
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Keywords: | Hetero Diels–Alder 1 3-Amino-alcohols Prozac Duloxetine |
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