2014-2013
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Highly Regioselective Synthesis of 3-Alkylthio-2-oxindoles via DABCO-catalyzed Allylic alpha-substitution of Morita-Baylis-Hillman Carbonates of Isatins with Various Thiols(Tetrahedron 2014, 70, 9191e9197

Graphic Abstract

 

ABSTRACT

The first Lewis base-catalysed allylic sulfuration of Morita-Baylis-Hillman (MBH) adducts derived from ketones (isatins) has been developed, which affords C3-quaternary oxindole derivatives bearing thio- group at 3-position in good to excellent yield (up to 98% yield) under mild reaction conditions. Significantly, the potential utility of the protocol also has been demonstrated by gram-scale synthesis of 3-alkylthio-2-oxindole (3ae), a low catalyst loading (0.3 mol %), and facile conversion of resulting product(3ad) into functionalized pyrrolidinone(5ad).