17422-71-8

Upstream product

• 34450-60-7 (Z)-3-iodobut-2-enoic acid 
• 41391-54-2 (tri-n-butylstannyl)-1,2-butadiene 
• 541-47-9 3-Methylbutenoic acid 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 79-03-8 propionyl chloride 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 60574-14-3 (E)-3-Methyl-5-oxo-hept-2-enoic acid methyl ester 
• 675-09-2 4,6-Dimethyl-2-pyron 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones

A number of 4-methyl-6-alkyl-α-pyrones were synthesized and characterized on the basis of 1H NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-α-pyrone, 4-methyl-6-pentyl-α-pyrone, 4-methyl-6-hexyl-α-pyrone, and 4-methyl-6-heptyl-α-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 μg/mL. 4-Methyl-6-hexyl-α- pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-α-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.

Synthesis of isocoumarins and α-pyrones via tandem Stille reaction/heterocyclization

A general route to α-pyrones and 3-substituted isocoumarins from (Z)-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c with various allenyl-tributyltin reagents in the presence of palladium acetate, triphenylphosphine, and tetrabutylammonium bromide in dimethylformamide provided good yields of the corresponding α-pyrones 3a-k or 3-substituted isocoumarins 5a-g via tandem Stille reaction and 6-endo-dig oxacyclization.

Formal ring-opening/cross-coupling reactions of 2-pyrones: Iron-catalyzed entry into stereodefined dienyl carboxylates

Open access: Despite the exceptional level of sophistication in cross-coupling chemistry, reactions of substrates that incorporate the leaving group as an integral part into a heterocyclic scaffold are scarce. The title reaction outlines the utility of this reaction format (see scheme; acac=acetylacetonate), provides a convenient entry into stereodefined diene carboxylates, and adds a new chapter to the field of iron catalysis. Copyright

Palladium-catalysed annulation reaction of allenyltins with β-iodo vinylic acids: Selective synthesis of α-pyrones

Palladium-catalysed regio- and stereoselective annulation of allenyl stannanes by β-iodo vinylic acids gives the corresponding α-pyrones in high yields. This annulation most probably proceeds through a Stille reaction/cyclisation sequence.