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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
Author(s) -
Tominaga Yoshinori,
Nomoto Kenichi,
Yoshioka Noriko
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380518
Subject(s) - chemistry , potassium carbonate , ring (chemistry) , dimethyl sulfoxide , medicinal chemistry , potassium , nitrogen , organic chemistry , stereochemistry
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.