Synthesis of some N-substituted isonicotinamides

✍ Scribed by Andreja Černigoj-Marzi; Slovenko Polanc; Marijan Kočevar

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 340 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340618

✦ Synopsis

Abstract

A one‐pot transformation of some cyclic 1,3‐dicarbonyls 1 with N‐(isonicotinoyl)glycine 2 and one‐carbon synthons in acetic anhydride to the corresponding N‐substituted isonicotinamides (pyridine‐4‐carbox‐amides) 7‐9 containing a fused pyran‐2‐one ring is described. Compound 8 was further converted with some nitrogen‐containing nucleophiles either to the corresponding quinoline‐2,5‐diones 10‐11 or 5‐hydra‐zonobenzopyran‐2‐ones 14‐15. Under more severe conditions the compound 8 gave with hydrazine 5‐hydrazonoquinoline derivative 12 or even 13. Hydrazoic acid transformed compound 8 to the pyrano‐[3,2‐c]azepine system 16. Diazotization of 1‐amino derivative 10 gave deaminated product 11.