Tetrahedron Letters

Regioselective synthesis of 4-alkylquinolines from quinoline via 1-ethoxycarbonyl-1, 2-dihydroquinoline-2-phosphonates

K Akiba, T Kasai, M Wada

Index: Akiba, Kin-ya; Kasai, Tetsuji; Wada, Makoto Tetrahedron Letters, 1982 , vol. 23, # 16 p. 1709 - 1712

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Citation Number: 13

Abstract

Abstract: l-Ethoxycarbonyl-1, 2-dihydroquinoline-2-phosphonates(L) were treated with n- butyllithium followed by alkyl halides to afford the corresponding 4-alkylated phosphor&es (2) with complete regioselectivity in 67-97s yields. The phosphonates (L) were converted to 4-alkylquinolines (a) in ca. 56% yields by treatment with sodium iodide in HMPA or by alkaline hydrolysis in aqueous ethanol.

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