Tetrahedron Letters

Regioselective synthesis of 4-alkylpyridines via 1, 4-dihydropyridine derivatives from pyridine

K Akiba, Y Iseki, M Wada

Index: Akiba, Kin-ya; Iseki, Yuji; Wada, Makoto Tetrahedron Letters, 1982 , vol. 23, # 4 p. 429 - 432

Full Text: HTML

Citation Number: 77

Abstract

Abstract N-Ethoxycarbonylpyridinium chloride (1) reacted with RCu· BF 3 at 4-position with almost complete regioselectivity (better than 99%) to afford the corresponding 1, 4- dihydropyridine derivatives (2) in high yields (81≈ 94%). The dihydropyridines were readily oxidized by oxygen to give 4-alkylpyridines (4: 38≈ 68% yields).

Related Articles:

Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants

[Robertson, Linsey; Hartley, Richard C. Tetrahedron, 2009 , vol. 65, # 27 p. 5284 - 5292]

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

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

Zn-promoted regio-and sequence-selective one-pot joining reactions of three components: vinylpyridines, alkyl iodides, and carbonyl compounds (or nitriles)

[Mineyama, Kenji; Maekawa, Hirofumi; Kohsaka, Akihiro; Yamamoto, Yoshimasa; Nishiguchi, Ikuzo Tetrahedron, 2009 , vol. 65, # 36 p. 7706 - 7711]

Facile synthesis of 4-substituted pyridines using grignard reagents

[Akiba, Kin-ya; Iseki, Yuji; Wada, Makoto Tetrahedron Letters, 1982 , vol. 23, # 38 p. 3935 - 3936]

Facile synthesis of 4-substituted pyridines using grignard reagents

[Akiba, Kin-ya; Iseki, Yuji; Wada, Makoto Tetrahedron Letters, 1982 , vol. 23, # 38 p. 3935 - 3936]

More Articles...