4.4 Article

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

Journal

TETRAHEDRON
Volume 64, Issue 9, Pages 2048-2056

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.12.044

Keywords

Knoevenagel reactions; circumdatin; pyrrolobenzodiazepine

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(S)-11-Thioxo-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5(10H)-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-2H-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. (c) 2007 Elsevier Ltd. All rights reserved.

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