New derivatives and ring systems of annulated pyrrolobenzo[1,4]diazepines

( S)-11-Thioxo-2,3,11,11a-tetrahydro-1 H-benzo[ e]pyrrolo[1,2- a][1,4]diazepine-5(10 H)-one was subsequently reacted with amino acid esters and base to give new 6:7:5:5, 6:7:5:6, and 6:5:7:7 ring systems. The 6:7:5:5 ring system, ( S)-11,12,13,13a-tetrahydro-2 H-benzo[ e]imidazo[2,1- c]pyrrolo[1,2-...

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Bibliographic Details
Published in:Tetrahedron 2008-02, Vol.64 (9), p.2048-2056
Main Authors: Schmidt, Andreas, Lindner, Anika Sabine, Shilabin, Abbas Gholipour, Nieger, Martin
Format: Article
Language:English
Subjects:
Circumdatin
Knoevenagel reactions
Pyrrolobenzodiazepine
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Summary:( S)-11-Thioxo-2,3,11,11a-tetrahydro-1 H-benzo[ e]pyrrolo[1,2- a][1,4]diazepine-5(10 H)-one was subsequently reacted with amino acid esters and base to give new 6:7:5:5, 6:7:5:6, and 6:5:7:7 ring systems. The 6:7:5:5 ring system, ( S)-11,12,13,13a-tetrahydro-2 H-benzo[ e]imidazo[2,1- c]pyrrolo[1,2- a][1,4]diazepine-3,9-dione, exhibits a considerable CH-acidity at position 2, which was exploited in Knoevenagel reactions, a Wittig reaction, enol ester formations, and methylations. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.12.044