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Synthesis of original benzo[g]quinoxaline-5,10-diones by bis-SRN1 methodology

✍ Scribed by Vincent Remusat; Thierry Terme; Armand Gellis; Pascal Rathelot; Patrice Vanelle

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
182 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new heterocyclic bioreductive bis‐alkylating agent, 2,3‐bis(chloromethyl)benzo[g]quinoxaline‐5,10‐dione, was prepared in a four‐steps synthesis. It was shown to react under electron transfer conditions with 2‐nitropropane anion by an bis‐S~RN~1 mechanism to give three C‐alkylation products in excellent yields. Extension of this bis‐S~RN~1 reaction to various nitronate or malonate anions and S‐centered anions led to a new class of potentially active benzo[g]quinoxaline‐5,10‐dione derivatives.

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