Synthesis of functionalized benzimidazole-butyrolactone dyads
authors Bouaziz, O; Amari, M; Bachar, R; Khier, N; Fodili, M; Paz, FAA; Talhi, O; Silva, AMS
nationality International
journal TETRAHEDRON LETTERS
author keywords Benzimidazole Butyrolactone; Dyads; NMR; Reaction intermediates; (E/Z)-Isomerism
keywords METHYLENE-GAMMA-BUTYROLACTONES; BRIDGEHEAD NITROGEN ATOM; HETEROCYCLIC-SYSTEMS; DERIVATIVES; ACID; THIAZOLO<3,2-A>BENZIMIDAZOL-3(2H)-ONES; INHIBITORS; PYRAZOLE; CHROMONE; POTENT
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.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4039
year published 2015
volume 56
issue 8
beginning page 1020
ending page 1024
digital object identifier (doi) 10.1016/j.tetlet.2015.01.039
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000349505600012
  ciceco authors
  impact metrics
journal analysis (jcr 2019):
journal impact factor 2.275
5 year journal impact factor 1.928
category normalized journal impact factor percentile 53.509
dimensions (citation analysis):
altmetrics (social interaction):



 


Apoio

1suponsers_list_ciceco.jpg