Synthesis and X-ray crystal structures of polyfunctionalized 4 H -chromene derivatives via tricomponent reaction with Knoevenagel adducts as intermediates in aqueous medium.
ZANIN, Lucas Lima; JIMENEZ, David Esteban Quintero; JESUS, Matheus Pereira de; DINIZ, Luan Farinelli; ELLENA, Javier; PORTO, André Luiz Meleiro.
ZANIN, Lucas Lima; JIMENEZ, David Esteban Quintero; JESUS, Matheus Pereira de; DINIZ, Luan Farinelli; ELLENA, Javier; PORTO, André Luiz Meleiro.
Abstract: Chromenes and their derivatives are an important class of compounds known for their biological prop- erties. In this study, synthetic methodologies were described to obtain 4 H -chromene derivatives. Two routes were investigated, the first being a bicomponent reaction using Knoevenagel adducts as reagents and the second using one-pot tricomponent reactions, both under microwave irradiation, using H 2 O as solvent and triethylamine as catalyst. Twenty 4 H -chromene derivatives were synthesized with 50-95% yields from aromatic aldehydes, 5,5-dimethyl-1,3-cyclohexadione and malononitrile or methyl cyanoac- etate, being further characterized by Fourier Transform Infrared and Nuclear Magnetic Resonance. We also report three crystal structures from the synthesized chromene derivatives, by single-crystal X-ray diffraction, showing the main supramolecular features of each structure ?a poorly unexplored approach involving this class of compounds so far.
@article={003005969,author = {ZANIN, Lucas Lima; JIMENEZ, David Esteban Quintero; JESUS, Matheus Pereira de; DINIZ, Luan Farinelli; ELLENA, Javier; PORTO, André Luiz Meleiro.},title={Synthesis and X-ray crystal structures of polyfunctionalized 4 H -chromene derivatives via tricomponent reaction with Knoevenagel adducts as intermediates in aqueous medium},journal={Journal of Molecular Structure},note={v. 1223, p. 129226-1-129226-10},year={2020}}