abstract
A two-step procedure transformation starting from the reaction of ortho-phenylenediamines on 2-acetylbutyrolactone 1 yielded (Z)-3-(1-aminoethylidene)butyrolactones 2, 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 dyads 3-5, respectively. The structures of compounds 2-5 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 systems 3-5 by X-ray diffraction studies. (C) 2015 Elsevier Ltd. All rights reserved.
keywords
METHYLENE-GAMMA-BUTYROLACTONES; BRIDGEHEAD NITROGEN ATOM; HETEROCYCLIC-SYSTEMS; DERIVATIVES; ACID; THIAZOLO<3,2-A>BENZIMIDAZOL-3(2H)-ONES; INHIBITORS; PYRAZOLE; CHROMONE; POTENT
subject category
Chemistry
authors
Bouaziz, O; Amari, M; Bachar, R; Khier, N; Fodili, M; Paz, FAA; Talhi, O; Silva, AMS
our authors
Filipe Alexandre Almeida Paz
Principal Researcheracknowledgements
Thanks are due to the University of Aveiro, Fundacao para a Ciencia e a Tecnologia (Portugal), EU, QREN, FEDER, COMPETE, for funding the Organic Chemistry Research Unit (project PEst-C/QUI/UI0062/2013), and the Portuguese National NMR Network (RNRMN). We would like to thank the General Directorate for Scientific Research and Technological Development-DGRSDT of Algeria for the financial support. O. Talhi also thanks the project New Strategies Applied to Neuropathological Disorders (CENTRO-07-ST24-FEDER-002034), co-funded by QREN, 'Mais Centro-Programa Operacional Regional do Centro' and EU, FEDER for his Post-doctoral position. We further wish to thank the Associated Laboratory CICECO (FCT grant PEst-C/CTM/LA0011/2013; FCOMP-01-0124-FEDER-037271) for funding the purchase of the single-crystal Xray diffractometer.