Peculiarities of the nitration of 2-methyl-4-methoxymethyl-5-cyano-6-pyridone in a mixture of HNO3 and H2SO4

Dihydrofuro[3,4-c]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin

“…The stereoselectivity of the aldolization−crotonization reaction has previously been reported to favor the formation of Z -stereoisomers. , Our observations for a sample of 12 in DMSO- d 6 in an experiment using a rotational nuclear Overhauser effect (ROESY) experiment are consistent with these results. The olefinic proton (δ = 7.08 ppm) and the pyridinethione 7-H (δ = 7.19 ppm) correlate strongly, indicating their close proximity.…”

“…Intermediate 8 was prepared by catalytic hydrogenation of compound 6 , in accordance with previously reported results . The lactam 9 was obtained by reaction of 4 with concentrated sulfuric acid (Scheme ) . Preparation of the corresponding thioxo-analogue 11 involved the reaction of 2-thiocyanoacetamide with 3 to give the thioxopyridine 10 .…”

“…30 The lactam 9 was obtained by reaction of 4 with concentrated sulfuric acid (Scheme 2). 31 Preparation of the corresponding thioxo-analogue 11 involved the reaction of 2-thiocyanoacetamide with 3 to give the thioxopyridine 10. The lactamization then proceeded under the same conditions and afforded 11 in moderate yields.…”

“…Compounds 17-19 employed various 5-membered nitrogen heterocycles (pyrrole, imidazole, and N-methylpyrrole, respectively) as furan replacements, but none of these compounds were active. A series of compounds with a benzene ring bearing a range of electron-donating and -withdrawing substituents at a geometrically similar 4-position were also prepared (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31). No activity was observed for any of these analogues irrespective of substitution.…”

“…(Z)-1-(Biphenyl-4-ylmethylene)-6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one (31). Yield 70%, yellow solid, mp > 300 °C.…”