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Synthesis and Spectroscopic Analysis of Novel 1<em>H</em>-Benzo[<em>d</em>]imidazoles Phenyl Sulfonylpiperazines

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Author(s): Amjad M. Qandil

Journal: Pharmaceuticals
ISSN 1424-8247

Volume: 5;
Issue: 5;
Start page: 460;
Date: 2012;
Original page

Keywords: phenyl sulfonylpiperazine | benzimidazole | mass spectrometry | NMR

ABSTRACT
A group of benzimidazole analogs of sildenafil, 3-benzimidazolyl-4-methoxy-phenylsulfonylpiperazines 2–4 and 3-benzimidazolyl-4-methoxy-N,N-dimethyl- benzenesulfonamide (5), were efficiently synthesized. Compounds 2–5 were characterized by NMR and MS and contrary to the reported mass spectra of sildenafil, the spectra of the piperazine-containing compounds 2–4 showed a novel fragmentation pattern leading to an m/z = 316. A mechanism for the formation of this fragment was proposed.
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