Manoj Patel, R. C. Fox, P. Taylor
Jan 29, 1996
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron
Abstract
Abstract The site of aminomethylation of N-unsubstituted 3-hydroxy-2-( 1H )-pyridinones and 3-hydroxy-4( 1H )-pyridinones, under Mannich reaction conditions, is directed by the hydroxyl group when this is unprotected and by the kelo group when the hydroxyl is protected as an ether. This offers a convenient route to a variety of Mannich base synthons useful in the synthesis of derivatives of these clinically important, bidentate, metal-ion chelators. This is exemplified by reactions of 3-hydroxy-2-( 1H )-pyridinone, 3-methoxy-2( 1H )-pyridinone, 2-hydroxymethyl- 5-hydroxy- 4( 1H ) pyridinone and 3- benzyloxy- 2- methyl-4( 1H )- pyridinone.