Synthesis of polycyclic nitrogen-containing heterocyclic: One pot formation of 1,6-naphthyridine ring system by reaction of amino-cyano-methylthio-heterocycles with dialkyl acetyeledicarboxylates

✍ Scribed by Yoshinori Tominaga; Kenichi Nomoto; Noriko Yoshioka

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 85 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380518

✦ Synopsis

Abstract

Reaction of 3‐amino‐3‐methylthio‐2‐cyanoacrylonitrile (1) with excess dimethyl acetylenedi‐carboxylate(DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave a novel tricyclic heterocycle, hexamethyl l__H__‐1,4,7‐triazaphenalene‐2,3,5,6,8,9‐hexacarboxylate (5a). When one equivalent of DMAD was used in this reaction, dimethyl 4‐amino‐3‐cyano‐2‐methylthiopyridine‐5,6‐dicarboxylate (3a), a key intermediate of 5a, was obtained.