Etude des reactions de srn1—partie 10 : Action de sulfanions sur les halogenures d'aryle fonctionnalises. synthese directe de benzothiophenes et thienopyridines |
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Authors: | Ren Beugelmans Michle Bois-Choussy Bernard Boudet |
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Institution: | Institut de Chimie des Substances Naturelles du CNRS, Gif-sur-Yvette 91190, France |
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Abstract: | Functionalized aromatic halides Ar1XY (Ar1 = C6H4, Y = OCH3, CONH2, CN, COCH3, CHO, COC6H5) undergo SRN1 reactions with sulphur anions -SR, either simple (R=C2H5, CH2C6H5) or functionalized (R = (CH2)2OH, (CH2)2CO2Et, CH2CO2Et). Products Ar1YS- formed from the fragmentation of the radical anion Ar1YSR- are related to the redox potential of the aryl moiety Ar1Y and with the energy of the bond S-R. In the heterocyclic series (Ar2 = pyridine, Ar3 = quinoline) a similar relationship appears but a competitive SN(Ar) reaction occurs for pyridine substrates bearing an electron withdrawing group. A direct synthesis of benzothiophen via SRN1 reaction and an improved synthesis of thienopyridines based on the SN(Ar) reaction are reported. |
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