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

…, C Pedregal, C Lamas, J Barluenga…

Index: 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

Full Text: HTML

Citation Number: 192

Abstract

Upon reaction with IPy2BF4, 4-substituted anilines give regioselectively the corresponding o- iodoanilines in nearly quantitative yield, in a process that can be carried out on a multigram scale. Palladium-catalyzed coupling of the resulting 2-iodoanilines with (trimethylsilyl) acetylene (TMSA), followed by efficient CuI-mediated nitrogen cyclization onto alkynes with concurrent elimination of the TMS substituent, allows a straightforward elaboration of 5- ...

~49%

~84%

~97%

~97%

~72%

~95%

~95%

~98%

~95%

~66%

~46%

~10%

~60%

~97%

~56%

Ruthenium-catalysed synthesis of indoles from anilines and t...

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

Ruthenium-catalyzed heteroannulation of anilines with alkano...

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

Synthesis of novel indole derivatives: variations in the Bar...

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

Diels-Alder reactions of 1, 5-dihydropyrano [3, 4-b] pyrrol-...

[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]