Abstract
Commercial dehydroacetic acid was converted into 4-hydroxy-6-methylpyridin-2(1H)-one (3), which was then condensed with several aliphatic aldehydes to produce seven new title compounds in variable yields (35–92%). Reaction of 3 with α,β-unsaturated aldehydes resulted in the formation of condensed pyran derivatives 4g’ and 4h’. A mechanism is proposed to explain the formation of such compounds. The effects of all methylpyridin-2(1H)-one derivatives on the development of the dicotyledonous species Ipomoea grandifolia and Cucumis sativus and the monocotyledonous species Sorghum bicolor were evaluated. At the dose of 6.7 × 10-8 mol a.i./g substrate the compounds showed some phytotoxic selectivity, being more active against the dicotyledonous species. These compounds can be used as lead structures for the development of more active phytotoxic products.
Highlights
Pyridin-2(1H)-ones are known to possess a range of biological activities such as analgesic, antifungal, antimalarial, antiinflammatory, antibacterial, anti-HIV, phytotoxic, antitumoral and Molecules 2009, 14 antiviral properties [1,2,3,4,5,6,7,8,9]
We have described the preparation of a variety of functionalized bis(pyridyl)methanes, starting from dehydroacetic acid
We have demonstrated that the condensation of 4-hydroxypyridone 3 with cinnamaldehydes results in the formation of pyran derivatives
Summary
Pyridin-2(1H)-ones are known to possess a range of biological activities such as analgesic, antifungal, antimalarial, antiinflammatory, antibacterial, anti-HIV, phytotoxic, antitumoral and Molecules 2009, 14 antiviral properties [1,2,3,4,5,6,7,8,9]. Fluridone and sapinopyridione are representative examples of pyridinones that possess phytotoxic activity [5,7]. This class of compounds has been used to formulate lead compounds for the synthesis of new pyridiones [1,3,4,12,13], including the bis(pyridyl)methanes, which present antitumoral activity [8,9]. In continuing our research in this direction, we report the synthesis of pyridone derivatives 4a-h and some studies on their phytotoxic activities
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