The preparation and manipulation of functionalized low molecular weight heteroaromatic compounds is of increasing importance for obtaining new more potent pharmaceuticals [1]. In particular, 3-sulfenyl indoles (4) and 2-sulfenyl pyrrole (5) are an important class of compounds due their activity towards the treatment of several deseases [2], and as inhibitors in medicinal chemistry [3]. Most of methods for their preparation are based on electrophilic aromatic sulfenylation, but a considerable number of them have been unsatisfactory because the procedures provide low yields of the desired products, and/or require harsh conditions that are incompatible with sensitive functional groups [4]. In the framework of our ongoing program in the development of Lewis acid-catalyzed reactions by CeCl [5], we have developed a new general and efficient methodology for the sulfenylation of indoles 1 and pyrroles 2 by N-(alkylthio)- and N-(arylthio)phthalimides (3) in the presence of our combination CeCl3.7H2O/NaI.

Novel and Efficient CeCl3.7H2O/NaI-Catalyzed Sulfenylation of Indoles and Pyrroles / R. Cipolletti, ; A, ; E. Marcantoni, ; A, ; L. Marsili, ; A, ; S. Menichetti, ; B, ; R. Properzi, ; Viglianisi, C.. - STAMPA. - (2011), pp. 882-882. (Intervento presentato al convegno XXIV Congresso Nazionale della Società Chimica Italiana tenutosi a Lecce nel 11-16 settembre 2011).

Novel and Efficient CeCl3.7H2O/NaI-Catalyzed Sulfenylation of Indoles and Pyrroles

MENICHETTI, STEFANO;VIGLIANISI, CATERINA
2011

Abstract

The preparation and manipulation of functionalized low molecular weight heteroaromatic compounds is of increasing importance for obtaining new more potent pharmaceuticals [1]. In particular, 3-sulfenyl indoles (4) and 2-sulfenyl pyrrole (5) are an important class of compounds due their activity towards the treatment of several deseases [2], and as inhibitors in medicinal chemistry [3]. Most of methods for their preparation are based on electrophilic aromatic sulfenylation, but a considerable number of them have been unsatisfactory because the procedures provide low yields of the desired products, and/or require harsh conditions that are incompatible with sensitive functional groups [4]. In the framework of our ongoing program in the development of Lewis acid-catalyzed reactions by CeCl [5], we have developed a new general and efficient methodology for the sulfenylation of indoles 1 and pyrroles 2 by N-(alkylthio)- and N-(arylthio)phthalimides (3) in the presence of our combination CeCl3.7H2O/NaI.
2011
XXIV Congresso Nazionale della Società Chimica Italiana, Lecce, Italy, 11-16 settembre 2011
XXIV Congresso Nazionale della Società Chimica Italiana
Lecce
R. Cipolletti, ; A, ; E. Marcantoni, ; A, ; L. Marsili, ; A, ; S. Menichetti, ; B, ; R. Properzi, ; Viglianisi, C.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1055066
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