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1. Homolytic substitution reactions of electron-rich pentatomic heteroaromatics by electrophilic carbon-centered radicals. Synthesis of alpha-heteroarylacetic acids

Author

Baciocchi, Enrico, Muraglia, Ester, and Sleiter, Giancarlo

Subjects
Substitution reactions -- Research, Heterocyclic compounds -- Research, Indole -- Research, Anti-inflammatory drugs -- Research, Biological sciences, Chemistry
Abstract

Homolytic substitutions of pyrrole, indole and some pyrrole derivatives were performed with ambiphilic and electrophilic carbon centered radicals. The efficiency of the reactions is attributed to the radicals prepared in DMSO by H2O2, Fe2+ and alpha-cyano, alpha-carbonyl- and alpha,alpha'-dicarbonylalkyl iodides. Using this process, a commercial antiinflammatory drug Tolmetin was synthesized by the reaction of 2-(p-methylbenzoyl)-N-methylpyrrole and .CH2CO2Et.

Published
1992

2. Halogenation and oxidation of 2,5-bis(ethoxycarbonyl)-3,4-dialkylpyrroles. A possible route to side-chain functionalized 3,4-dialkylpyrroles

Author

Baciocchi, Enrico, Muraglia, Ester, and Sleiter, Giancarlo

Subjects
Halogenation -- Research, Oxidation-reduction reaction -- Research, Pyrrole -- Research, Biological sciences, Chemistry
Abstract

Diethyls 3,4-dimethylpyrrole-2,5-dicarboxylate and 3-ethyl-4-methylpyrrole-2, 5-dicarboxylate undergo efficient halogenation and oxidation reactions with N-bromo- and chlorosuccinimide in CCl4 and cerium(IV) ammonium nitrate (CAN), respectively. These hydrogen atom and electron transfer reactions suggest that diethyl 3,4-dialkylpyrrole-2,5-dicarboxylates provide substrate properties that facilitate beta-alkyl group side-chain additions. N-bromosuccinimides promote the functionalization of the two alkyl units in the parent compound while CAN and PCl5 only allow monofunctionalization.

Published
1992

13. Electrochemically Induced N-Alkylation of Pyrroles

Author

Feroci, Marta, Inesi, Achille, Rossi, Leucio, and Sleiter, Giancarlo

Abstract

Electrochemically generated tetraethylammonium peroxydicarbonate (TEAPC) and tetraethylammonium carbonate (TEAC) react under very mild conditions with pyrroles affording, after addition of a suitable alkylating agent, the corresponding N-alkylated pyrroles in high yields. C-Alkylated pyrroles have not been isolated in any case reported.

Published
1999
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18. CHIMICA ORGANICA

Author

Lucio Pellacani, Sleiter, Giancarlo, and Tardella, Paolo Antonio

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