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 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.