75421-96-4Relevant academic research and scientific papers
Preparation of sulfenyl pyrroles
Gillis, H. Martin,Greene, Lana,Thompson, Alison
experimental part, p. 112 - 116 (2009/06/18)
Sulfenyl groups are attracting interest as masking/protecting groups for pyrroles. A facile one-step synthesis of sulfenyl pyrroles, involving the reaction of pyrroles with N-(aryl- and alkylthio)phthalimides in the presence of MgBr2, is reported and the methodology extends to include sulfinyl pyrroles. The one-step procedure gives good yields and is more efficient and practical than current multistep protocols to sulfenyl pyrroles that involve thiocyanato pyrrolic intermediates. A convenient procedure for the synthesis of N-(aryl- and alkylthio)phthalimides is also reported. Georg Thieme Verlag Stuttgart.
Synthesis and Rearrangement of Pyrrolyl Sulfides and Sulfones
DeSales, Javier,Greenhouse, Robert,Muchowski, Joseph M.
, p. 3668 - 3672 (2007/10/02)
A general synthesis of 3-pyrrolyl sulfides was developed on the basis of the triphenylphosphine-iodine-sodium iodide reduction of the sulfoxides, which in turn were obtained by the acid-mediated rearrangement of the corresponding 2-sulfinylpyrroles.Methods were also devised for the reduction of 2-(alkylsulfinyl)pyrroles to the sulfides. 2-Pyrrolyl and 3-pyrrolyl sulfides were shown to undergo acid-induced equilibration under mild conditions.With trifluoroacetic acid in dichloromethane solution, at room temperature, the equilibrium always was in favor of the 2-isomer and the interconversion appeared to be intramolecular. 2-(Methylsulfonyl)pyrrole and 2-(phenylsulfonyl)pyrrole were transformed into the 3-substituted isomers when heated under strongly acidic conditions.
Antidiabetic pyrrolecarboxylic acids
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, (2008/06/13)
Certain pyrrolecarboxylic and pyrroleacetic acid derivatives substituted on the pyrrole ring with thioether groups, acyl groups, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzyl or halo and optionally substituted on the pyrrole nitrogen with alkyl, and the pharmaceutically acceptable salts thereof, are useful in lowering the blood glucose levels of hyperglycemic animals.
Synthesis and Rearrangement of 2-(Arylsulfinyl)- and 2-(Alkylsulfinyl)pyrroles
Carmona, Olga,Greenhouse, Robert,Landeros, Rosita,Muchowski, Joseph M.
, p. 5336 - 5339 (2007/10/02)
Pyrrole and N-methylpyrrole reacted with aryl- and alkylsulfinyl chlorides, at 0 deg C, to give the corresponding 2-sulfinylpyrroles as the major products only when contact of the products with the liberated hydrogen chloride was minimized or eliminated.If this precaution was not taken, the 3-sulfinylpyrroles were the principle products.In contrast, N-(phenylsulfinyl)succinimide (2a) reacted, at room temperature, with a variety of pyrroles to produce the 2-phenylsulfinyl compounds in good yields.The 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrroles undergo a remarkably facile acid-promoted rearrangement to the isomeric 3-sulfinylpyrroles.This transposition is, at least in part, an intermolecular process as demonstrated by crossover experiments.
