An expedient synthesis of 7-O-functionalised pyrrolo [2, 1-c][1, 4] benzodiazepine-5, 11-diones

H Madani, AS Thompson, MD Threadgill

Index: Madani, Hadi; Thompson, Andrew S; Threadgill, Michael D Tetrahedron, 2002 , vol. 58, # 40 p. 8107 - 8111

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Citation Number: 8

Abstract

An efficient synthetic route to 7-hydroxypyrrolo [2, 1-c][1, 4] benzodiazepine-5, 11-dione, an important potential ligand for the DNA minor groove, has been developed. Simultaneous reduction of nitro and hydrogenolysis of the O-benzyl in N-(5-benzyloxy-2-nitrobenzoyl)-l- proline methyl ester, followed by thermal cyclisation, gave 7-hydroxypyrrolo [2, 1-c][1, 4] benzodiazepine-5, 11-dione. This was alkylated to give the prop-2-ynyl ether. Reaction of ...