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Synthesis and characterization of 2-chloro-3-benzylthiopyrrolo[1,2-a]- benzimidazol-1-one and 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one.

The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography.

Identiferoai:union.ndltd.org:unt.edu/info:ark/67531/metadc4415
Date12 1900
CreatorsHuang, Shih-Huang
ContributorsRichmond, Michael, Mason, Diana
PublisherUniversity of North Texas
Source SetsUniversity of North Texas
LanguageEnglish
Detected LanguageEnglish
TypeThesis or Dissertation
FormatText
RightsPublic, Copyright, Huang, Shih-Huang, Copyright is held by the author, unless otherwise noted. All rights reserved.

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