Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4-and 1,6-Aza-Conjugate Additions/Heterocyclizations
authors Bouchama, A; Hassaine, R; Talhi, O; Taibi, N; Mendes, RF; Paz, FAA; Bachari, K; Silva, AMS
nationality International
journal SYNLETT
author keywords styrylchromones; ethanediamine; chromenopyridodiazepinones; one-pot synthesis; tandem reaction; aza-conjugated addition
keywords ANTIOXIDANT ACTIVITY; CARCINOMA-CELLS; 2-STYRYLCHROMONES; HYBRIDS; DERIVATIVES; REACTIVITY; DESIGN; AGENTS; CYTOTOXICITY; SCAVENGERS
abstract We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleophilic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane-1,2-diamine to the alpha,beta-unsaturated (3-oxoprop-1-en-1-yl) and the alpha,beta,gamma,delta-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.
publisher GEORG THIEME VERLAG KG
issn 0936-5214
year published 2018
volume 29
issue 7
beginning page 885
ending page 889
digital object identifier (doi) 10.1055/s-0037-1609201
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000429998900006
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journal impact factor 2.369
5 year journal impact factor 2.018
category normalized journal impact factor percentile 58.772
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