Synthesis of Substituted 1,2-Dihydro-2-imino-7-methyl-1,6(6H)-naphthyridin-5-ones

✍ Scribed by Ivanov, Ivo Christov ;Stoyanov, Edmont Vassilev ;Denkova, Pavletta Stoyanova ;Dimitrov, Valentin Stefanov

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 470 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970822

✦ Synopsis

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(6__H__)‐naphthyridin‐5‐ones 7a–p which have been shown by means of ^1^H‐NMR and ^1^H‐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.