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

Citation
Y. Tominaga et al., Synthesis of polycyclic nitrogen-containing heterocyclic [1]: One pot formation of 1,6-naphthyridine ring system by reaction of amino-cyano-methylthio-heterocycles with dialkyl acetyeledicarboxylates, J HETERO CH, 38(5), 2001, pp. 1135-1141
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1135 - 1141
Database
ISI
SICI code
0022-152X(200109/10)38:5<1135:SOPNH[>2.0.ZU;2-#
Abstract
Reaction of 3-amino-3-methylthio-2-cyanoacrylonitrile (1) with excess dimet hyl acetylenedicarboxylate(DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave a novel tricyclic heterocycle, hexamethyl 1H-1,4,7- triazaphenalene-2,3,5,6,8,9-hexacarboxylate (5a). When one equivalent of DM AD was used in this reaction, dimethyl 4-amino-3-eyano-2-methylthiopyridine -5,6-dicarboxylate (3a), a key intermediate of 5a, was obtained.