I. C. Ivanov, E. Stoyanov, P. Denkova
Aug 1, 1997
Citations
0
Influential Citations
7
Citations
Journal
Liebigs Annalen
Abstract
Vilsmeier formylation of the 4-amino-2-pyridinones 4a–d leads to the formation of the corresponding 3-carbaldehydes 5a–d (the diformylated product 8 is isolated as a by-product). A cyclizing Knoevenagel reaction of 5 with CH-acidic nitriles 6 in the presence of piperidine gives substituted 2-imino-1,6(6H)-naphthyridin-5-ones 7a–p which have been shown by means of 1H-NMR and 1H-NOE measurements not to rearrange to 9. The products 7 are resistant against hydrolysis and only the ester group can be hydrolysed to an acid, 7q. Compounds 7c, d, f display in vitro antituberculosis activity.