RESUMO
A simple, environmentally acceptable, a one-pot method, which is efficient, inexpensive, and rapid, afforded excellent yields of the 4H-chromeme derivatives 5 and 6 from a three-component reaction of dimedone, arylaldehdes 2a-b, and malononitrile and a two-component reaction of bisdimedones 3a-b and malononitrile, respectively. Refluxing ethanolic piperidine was used as the catalyst for the 10-min reactions. A one-pot reaction of benzylidenemalononitrile, instead of malononitrile, with bisdimedones 3a-b, using the aforementioned reaction, also provided the 4H-chromene derivative 5 in excellent yield. The structures of the newly synthesized compounds were elucidated by elemental analyses, X-ray crystallography, and a variety of spectroscopic methods, including proton and carbon nuclear magnetic resonance spectroscopy (1H-NMR and 13C-NMR, respectively), correlation spectroscopy (COSY), heteronuclear single quantum coherence spectroscopy (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC), and mass spectrometry (MS). The inhibitory effects of the 4H-chromeme derivatives 5 and 6 on the in vitro growth of human tumor cell and normal cell lines were greater than that of the reference drug doxorubicin.