[Reaction of pyridinium and quinolinium salts having the leaving group at the 2- or 4-position with active methylene compounds].
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.
Fujita
Reiko
R
Tohoku Pharmaceutical University, Sendai City, Japan. refujita@tohoku-pharm.ac.jp
Hoshino
Masato
M
Tojyo
Yusuke
Y
Kimura
Atsushi
A
Hongo
Hiroshi
H
D002625:Chemistry, Organic; D003512:Cyclohexanones / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D055601:Organic Chemistry Phenomena; D011726:Pyridinium Compounds / Q000737:chemistry*; D011806:Quinolinium Compounds / Q000737:chemistry*
D003512:Cyclohexanones; D008314:Malonates; D009570:Nitriles; D011726:Pyridinium Compounds; D011806:Quinolinium Compounds; C004636:1,3-cyclohexanedione; C000945:dicyanmethane; C005230:methyl malonate