M. Mizuno, M. Yamashita, Y. Sawai
Sep 11, 2006
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron
Abstract
Abstract Convenient and efficient syntheses of ethyl 4-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate ( 1d ) and 10-(3,4-dimethoxyphenyl)-7,8-dimethoxy-2 H -pyridazino[4,5- b ]quinolin-1-one ( 1e ), metabolites of TAK-603 ( 1 ), have been achieved. Use of the methanesulfonyl as a protective group of the phenolic hydroxy for Friedel–Crafts reaction enabled a new simpler synthetic route of 1d in high yield. Chloromethyl derivative ( 23 ) was converted to formyl derivative ( 32 ) using the Krohnke reaction, followed by cyclization with hydrazine, which formed a novel compound 1e .