Synthesis of original benzo[ g ]quinoxaline‐5,10‐diones by bis‐S RN 1 methodology

Synthesis of original benzo[ g ]quinoxaline‐5,10‐diones by bis‐S RN 1 methodology

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 e...

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Veröffentlicht in:Journal of heterocyclic chemistry 2004-03, Vol.41 (2), p.221-225
Hauptverfasser: Remusat, Vincent, Terme, Thierry, Gellis, Armand, Rathelot, Pascal, Vanelle, Patrice
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container_issue 2
container_start_page 221
container_title Journal of heterocyclic chemistry
container_volume 41
creator Remusat, Vincent
Terme, Thierry
Gellis, Armand
Rathelot, Pascal
Vanelle, Patrice
description 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.
doi_str_mv 10.1002/jhet.5570410212
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title Synthesis of original benzo[ g ]quinoxaline‐5,10‐diones by bis‐S RN 1 methodology
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