Tetrahedron Letters

Efficient synthesis of substituted quinolines through intramolecular addition of aryl anion to carbonyl carbon

Y Kobayashi, J Igarashi, C Feng

Index: Kobayashi, Yuichi; Igarashi, Junji; Feng, Chao; Toshifumi; Tojo Tetrahedron Letters, 2012 , vol. 53, # 29 p. 3742 - 3745

Full Text: HTML

Citation Number: 6

Abstract

Substituted quinolines were synthesized in three steps from the Boc amides of substituted 2- iodoanilines and alkyl vinyl ketones. This method consists of (1) N-Michael addition of the Boc amide of 2-iodoaniline to alkyl vinyl ketone in the presence of Cs2CO3 in MeCN;(2) I– Mg exchange of the adduct with 3.5 equiv of i-PrMgCl· LiCl, and (3) acid-catalyzed reaction (excess AcCl in EtOH) of the resulting alcohol. Six examples are given with good yields.

Related Articles:

Microwave-assisted synthesis of 3-substituted indoles via intramolecular arene–alkene coupling of o-iodoanilino enamines

[Lee, Won-Il; Jung, Jong-Wha; Sim, Jaehoon; An, Hongchan; Suh, Young-Ger Tetrahedron, 2013 , vol. 69, # 35 p. 7211 - 7219]

Fluorosulfonyl-substituted xanthines as selective irreversible antagonists for the A1-adenosine receptor

[Dhanak, Dashyant; Reese, Colin B. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 2181 - 2186]

Intramolecular carbonickelation of alkenes

[Lhermet, Rudy; Durandetti, Muriel; Maddaluno, Jacques Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 710 - 716]

Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins

[Kasaya, Yayoi; Hoshi, Kosuke; Terada, Yukiyoshi; Nishida, Atsushi; Shuto, Satoshi; Arisawa, Mitsuhiro European Journal of Organic Chemistry, 2009 , # 27 p. 4606 - 4613]

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

[Clark; Muchowski; Fisher; Flippin; Repke; Souchet Synthesis, 1991 , # 10 p. 871 - 878]

More Articles...