Synthesis of 5,6‐dihydro‐4H‐pyrrolo[1,2‐a][1,4]benzodiazepine and 10,11‐dihydro‐5H,12H‐pyrrolo[2,1‐c][1,4]benzodiazocine derivatives via cyclization of 2‐aminomethylpyrroles

Abstract

We have synthesized pyrrolo[1,2‐α][1,4]benzodiazepine 6 and pyrrolo[2,1‐c][1,4]benzodiazocines 12 and 13 from the corresponding 1‐arylpyrrole 1d and 1‐benzylpyrroles 7a and 7b by routes involving four and five steps, respectively.

An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines

“…Within the framework of their scientific interests regarding the synthesis of nitrogen containing tricyclic compounds of potential pharmaceutical value, Korakas and Varvounis [89,90] presented the preparation of PBDs 255 and 256 from 1-arylpyrroles 250a , b (Scheme 46). In the first step, pyrroles 250a , b were subjected to Mannich reaction conditions to afford the respective dimethylamino-methylpyrroles 251a , b which were treated with methyl iodide to produce the corresponding quaternary ammonium salts 252a , b .…”

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

“…Therefore, there is a need to introduce new and more efficient methods in order to develop the synthesis of medium-sized rings in the pharmaceutical industry. Interesting biological activities are shown by compounds containing five or six membered heterocyclic rings fused to diazocines [28,29,30,31,32,33,34]. Compound 3 , a potent and orally bioavailable Smac mimetic, inhibits cell growth and induces apoptosis in cancer cells and has been shown to be a potent antagonist of inhibitor of apoptosis proteins (IAPs).…”