Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations

• Published in: Synlett 2018-04, Vol.29 (7), p.885-889
• Main Authors: Bouchama, Abdelghani, Hassaine, Ridha, Talhi, Oualid, Taibi, Nadia, Mendes, Ricardo F., Almeida Paz, Fillipe A., Bachari, Khaldoun, Silva, Artur M. S.
• Format: Article
• Language: English
• Subjects: letter
• ISSN: 0936-5214; 1437-2096
• DOI: 10.1055/s-0037-1609201

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 α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-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.