Synthesis of functionalized benzimidazole–butyrolactone dyads. Issue 8 (18th February 2015)

• Record Type: Journal Article
• Authors: Bouaziz, Omar; Amari, Mohamed; Bachar, Rebat; Khier, Nawal; Fodili, Mokhtar; Almeida Paz, Filipe A.; Talhi, Oualid; Silva, Artur M.S.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 8(2015)
• Page Start: 1020
• Page End: 1024
• Publication Date: 2015-02-18
• Subjects: Benzimidazole -- Butyrolactone -- Dyads -- NMR -- Reaction intermediates -- (E/Z)-Isomerism; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.039
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The one-step synthesis of ( Z )-3-(1-aminoethylidene)butyrolactones is reported. A new series of benzimidazole–, benzimidazolone–, or benzimidazole-2-thione–butyrolactone conjugate is disclosed. ( Z )-Configuration of iminoamine intermediates established by X-ray diffractometry. Abstract: A two-step procedure transformation starting from the reaction of ortho -phenylenediamines on 2-acetylbutyrolactone1 yielded ( Z )-3-(1-aminoethylidene)butyrolactones2, which were treated with either N, N -dimethylformamide dimethyl acetal, triphosgene, or carbon disulfide under different reaction conditions to produce a new series of benzimidazole–, benzimidazolone–, or benzimidazole-2-thione–butyrolactone dyads3 –5, respectively. The structures of compounds2 –5 were established by NMR and mass spectrometry. The isolation of important reaction intermediates as single-crystals allowed the determination of the ( Z )-configuration in the resulting conjugate heterocyclic systems3 –5 by X-ray diffraction studies.