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  • [Reaction of pyridinium and quinolinium salts having the leaving group at the 2- or 4-position with active methylene compounds].

[Reaction of pyridinium and quinolinium salts having the leaving group at the 2- or 4-position with active methylene compounds].

Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan (2006-02-08)
Reiko Fujita, Masato Hoshino, Yusuke Tojyo, Atsushi Kimura, Hiroshi Hongo
ABSTRACT

The reactions of 2- or 4-cyanopyridinium salts with active methylene compounds such as dimethyl malonate, malononitrile, and cyclohexane-1,3-dione affording 2- or 4-(substituted methylene) pyridines are described. Similar reactions of 4-cyano-2-methylthiopyridinium and 4-cyano-2-methylthioquinolinium salts, both of which have two leaving groups, were readily prepared from 4-cyano-1-methyl-2(1H)-pyridone and 4-cyano-1-methyl-2(1H)-quinolone via 4-cyano-1-methyl-2(1H)-thiopyridone and 4-cyano-1-methyl-2(1H)-thioquinolone in two steps, proceeding at the 2- and/or 4-positions on the pyridine or quinoline rings.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,3-Cyclohexanedione, 97%
Sigma-Aldrich
Dimethyl malonate, 98%
Sigma-Aldrich
Dimethyl malonate, purum, ≥96.0% (GC)