YAKUGAKU ZASSHI 2006-02-01

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

Reiko Fujita, Masato Hoshino, Yusuke Tojyo, Atsushi Kimura, Hiroshi Hongo

Index: Yakugaku Zasshi 126(2) , 99-108, (2006)

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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.