resumo
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.
palavras-chave
ANTIOXIDANT ACTIVITY; CARCINOMA-CELLS; 2-STYRYLCHROMONES; HYBRIDS; DERIVATIVES; REACTIVITY; DESIGN; AGENTS; CYTOTOXICITY; SCAVENGERS
categoria
Chemistry
autores
Bouchama, A; Hassaine, R; Talhi, O; Taibi, N; Mendes, RF; Paz, FAA; Bachari, K; Silva, AMS
nossos autores
agradecimentos
Thanks are due to University of Aveiro and FCT/MEC for financial support to the QOPNA research project (FCT UID/QUI/00062/2013), to the CICECO-Aveiro Institute of Materials (POCI-01-0145-FEDER-007679; FCT UID/CTM/50011/2013), financed by national funds, and, when appropriate, co-financed by FEDER under the PT2020 Partnership Agreement, and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development (DGRSDT) of Algeria and Agence Thematique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005. We further wish to thank CICECO for funding the purchase of the single-crystal Xray diffractometer.