| Abstrakt: |
Bromination of 2methylfuropyridines 1adMegave the 3bromo derivatives 2ad, while the 2cyano compounds 1adCNresulted in the recovery of the starting compounds. Nitration of 1adMeand 1adCNdid not yield the corresponding nitro derivative, except for 1cCNgiving 3nitro derivative 3c in 7 yield. NOxidation of 1adMeand 1bdCNwith mchloroperbenzoic acid yielded the Noxides 4adMeand 4bdCN, whereas 1aCNdid not afford the Noxide. Cyanation of Noxides 4adMeand 4bdCNwith trimethylsilyl cyanide gave the corresponding αcyanopyridine compounds 5adMeand 5bdCN. Chlorination of 4adMeand 4bdCNwith phosphorus oxychloride also gave the αchloropyridine compounds 6bdMeand 6bdCN, accompanying formation of γchloropyridine 6aMe, 6′bMeand 6′bCN, βchloropyridine 6′bCN, and αchloropyridine derivatives 6′cMeand 6′cCN. Acetoxylation of 4adMeand 4bdCNwith acetic anhydride yielded αacetoxypyridine compounds 7aMeand 7bCN, pyridone compounds 11dMe, 11cCNand 11dCN, 3acetoxy compounds 8, 9b, 9c, and 2acetoxymethyl derivatives 10band 10c. |
Plný text