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Selectfluor‐Mediated N‐Methylation, N‐Methylenesulfonylmethylation and Methylenethiomethylation of Isatins in Dimethyl Sulfoxide
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Abstract
Dimethyl sulfoxide as a reagent and solvent in Selectfluor mediated transformations of isatin is reported. The transformations include
N
‐methylation and
N
‐methylenesulfonylmethylation of isatin at 100 °C whereas
N
‐methylenethiomethylation was observed at 140 °C in addition to
N
‐methylation and
N
‐methylenesulfonylmethylation of isatins. Electron withdrawing and releasing substituents on isatin were tolerated. Interestingly, dual (
N
‐ and
C
−)methylenethiomethylation was observed in case of 7‐Bromo‐ and 7‐Iodo isatins at 140 °C. This protocol efficiently afforded various isatin analogs using DMSO/Selectfluor system.
Title: Selectfluor‐Mediated N‐Methylation, N‐Methylenesulfonylmethylation and Methylenethiomethylation of Isatins in Dimethyl Sulfoxide
Description:
Abstract
Dimethyl sulfoxide as a reagent and solvent in Selectfluor mediated transformations of isatin is reported.
The transformations include
N
‐methylation and
N
‐methylenesulfonylmethylation of isatin at 100 °C whereas
N
‐methylenethiomethylation was observed at 140 °C in addition to
N
‐methylation and
N
‐methylenesulfonylmethylation of isatins.
Electron withdrawing and releasing substituents on isatin were tolerated.
Interestingly, dual (
N
‐ and
C
−)methylenethiomethylation was observed in case of 7‐Bromo‐ and 7‐Iodo isatins at 140 °C.
This protocol efficiently afforded various isatin analogs using DMSO/Selectfluor system.
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