Synthesis of a Pyrrolo [1, 4] Benzodiazepinequinone

…, CR Centella, JA Valderrama

Index: Tapia, Ricardo A.; Centella, Cesar R.; Valderrama, Jaime A. Synthetic Communications, 1999 , vol. 29, # 12 p. 2163 - 2168

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Citation Number: 8

Abstract

Abstract Condensation of 3, 6-dimethoxy-2-nitrobenzoyl chloride with L-proline methyl ester afforded amide 4, which underwent reductive cyclization with iron (II) sulfate and ammonium hydroxide to yield pyrrolobenzodiazepine 5. Oxidation of 5 with ammonium cerium (IV) nitrate led to the new heterocyclic quinone 6 in 53% overall yield.