Different 2-sulfonylaminoaryl diselenides substituted with electron-withdrawing or -donating groups are transformed in one pot into benzo[b][1,4]selenazines. The reaction uses a substoichiometric amount of Cu(OTf)2, and the mechanism involves a base-mediated 1,4-elimination at selenium with the generation of an o-iminoselenoquinone and a 2-sulfonylaminoselenolate anion. The former is a dienic species that can react with electron-rich dienophiles to give the target cycloadducts. The latter is oxidised by air back to the starting diselenide, allowing its complete consumption. A preliminary investigation of the GPx-like activity of a selected selenazine is also described.

A One-Pot Access to Benzo[b][1,4]selenazines from 2-Aminoaryl Diselenides / Menichetti, S; Capperucci, A; Tanini, D; Braga, Al; Botteselle, Gv; Viglianisi, C. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2016), pp. 3097-3102. [10.1002/ejoc.201600351]

A One-Pot Access to Benzo[b][1,4]selenazines from 2-Aminoaryl Diselenides

MENICHETTI, STEFANO;CAPPERUCCI, ANTONELLA;TANINI, DAMIANO;VIGLIANISI, CATERINA
2016

Abstract

Different 2-sulfonylaminoaryl diselenides substituted with electron-withdrawing or -donating groups are transformed in one pot into benzo[b][1,4]selenazines. The reaction uses a substoichiometric amount of Cu(OTf)2, and the mechanism involves a base-mediated 1,4-elimination at selenium with the generation of an o-iminoselenoquinone and a 2-sulfonylaminoselenolate anion. The former is a dienic species that can react with electron-rich dienophiles to give the target cycloadducts. The latter is oxidised by air back to the starting diselenide, allowing its complete consumption. A preliminary investigation of the GPx-like activity of a selected selenazine is also described.
2016
3097
3102
Menichetti, S; Capperucci, A; Tanini, D; Braga, Al; Botteselle, Gv; Viglianisi, C
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1055328
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