Tetrahedron

Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

CS Cho, JH Kim, TJ Kim, SC Shim

Index: Cho, Chan Sik; Kim, Jin Hwang; Kim, Tae-Jeong; Shim, Sang Chul Tetrahedron, 2001 , vol. 57, # 16 p. 3321 - 3329

Full Text: HTML

Citation Number: 69

Abstract

Anilines react with alkanolammonium chlorides in an aqueous medium (H2O–dioxane) at 180° C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2· 2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2· 2H2O is necessary for the effective ...

Related Articles:

Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin (II) chloride dihydrate

[Cho, Chan Sik; Lim, Hyo Kyun; Shim, Sang Chul; Kim, Tae Jeong; Choi, Heung-Jin Chemical Communications, 1998 , # 9 p. 995 - 996]

Efficient reagents for the synthesis of 5-, 7-, and 5, 7-substituted indoles starting from aromatic amines: Scope and limitations

[Ezquerra, Jesus; Pedregal, Concepcion; Lamas, Carlos; Barluenga, Jose; Perez, Marta; Garcia-Martin, Miguel Angel; Gonzalez, Jose M. Journal of Organic Chemistry, 1996 , vol. 61, # 17 p. 5804 - 5812]

Synthesis of novel indole derivatives: variations in the Bartoli reaction

[Dobbs, Adrian P.; Voyle, Martyn; Whittall, Neil Synlett, 1999 , # 10 p. 1594 - 1596]

Diels-Alder reactions of 1, 5-dihydropyrano [3, 4-b] pyrrol-5 (1H)-ones, pyrrole-2, 3-quinodimethane analogues; a new synthesis of indoles

[Mark Jackson; Moody, Christopher J. Tetrahedron, 1992 , vol. 48, # 36 p. 7447 - 7466]

Titanocene-based method for indole synthesis

[Journal of the American Chemical Society, , vol. 120, # 13 p. 3068 - 3073]

More Articles...