106531-53-7Relevant articles and documents
Furopyridines. V. A Simple Synthesis of Furopyridine and Its 2- and 3-Methyl Derivatives
Morita, Hiroyuki,Shiotani, Shunsaku
, p. 549 - 552 (2007/10/02)
A simple synthesis of furopyridine and its 2- and 3-methyl derivatives from ethyl 3-hydroxyisonicotinate (2) is described.The hydroxy ester 2 was O-alkylated with ethyl bromoacetate or ethyl 2-bromopropionate to give the diester 3a or 3b.Cyclization of compound 3a afforded ethyl 3-hydroxyfuropyridine-2-carboxylate (4) which was hydrolyzed and decarboxylated to give furopyridin-3(2H)-one (5a).Cyclization of 3b gave the 2-methyl derivative 5b.Reduction of 5a and 5b with sodium borohydride yielded the corresponding hydroxy derivative 6a and 6b, respectively, which were dehydrated with phosphoric acid to give furopyridine (7a) and its 2-methyl derivative 7b. 4-Acetylpyridin-3-ol (8) was O-alkylated with ethyl bromoacetate to give ethyl 2-(4-acetyl-3-pyridyloxy)acetate (9).Saponification of compound 9, and the subsequent intramolecular Perkin reaction gave 3-methylfuropyridine (10).Cyclization of 9 with sodium ethoxide gave 3-methylfuropyridine-2-carboxylic acid, which in turn was decarboxylated to give compound 10.
