A convenient method for the regioselective synthesis of 4-alkyl (aryl) pyridines using pyridinium salts.

K Akiba, Y Iseki, M Wada

Index: Akiba, Kin-ya; Iseki, Yuji; Wada, Makoto Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1994 - 1999

Full Text: HTML

Citation Number: 67

Abstract

RCu· BF 3 reacted with 1-ethoxycarbonylpyridinium chloride at the 4-position with almost complete regio-selectivity (> 99%) to afford the corresponding 1, 4-dihydropyridine derivatives in high yields (81–94%). The dihydropyridines were oxidized by oxygen to give 4- alkyl (aryl) pyridines (38–68%). Grignard reagents also reacted with 1-t- butyldimethylsilylpyridinium triflate with almost complete regioselectivity (> 99%) to afford ...