Tetrahedron

New Syntheses of Substituted Pyridines via Bromine–Magnesium Exchange

F Trécourt, G Breton, V Bonnet, F Mongin, F Marsais…

Index: Trecourt, Francois; Breton, Gilles; Bonnet, Veronique; Mongin, Florence; Marsais, Francis; Queguiner, Guy Tetrahedron, 2000 , vol. 56, # 10 p. 1349 - 1360

Full Text: HTML

Citation Number: 133

Abstract

Bromine–magnesium exchange using iPrMgCl in THF at room temperature on 2-, 3-and 4- bromopyridines allowed the synthesis of various functionalized pyridines. The methodology was successfully used for the synthesis of 4-azaxanthone. Moreover, single exchange reactions observed on 2, 6-, 3, 5-, 2, 3-and 2, 5-dibromopyridines, with complete regioselectivity in the case of 2, 3-and 2, 5-dibromopyridines, afforded substituted ...

~87%

~46%

~10%

~80%

~52%

~30%

~28%

~77%

~65%

~41%

~94%

~95%

~40%

~44%

~49%

~15%

Regiocontrolled deprotonative-zincation of bromopyridines us...

[Imahori; Uchiyama; Sakamoto; Kondo Chemical Communications, 2001 , # 23 p. 2450 - 2451]

Synthesis of “Acetylene-Expanded” Tridentate Ligands

[Holmes, Brian T.; Pennington, William T.; Hanks Molecules, 2002 , vol. 7, # 5 p. 447 - 455]

Homoleptic Zincate??Promoted Room??Temperature Halogen–Metal...

[Chemistry - A European Journal, , vol. 16, # 41 p. 12425 - 12433]

Deprotonative Metalation of Chloro??and Bromopyridines Using...

[Chemistry - A European Journal, , vol. 17, # 47 p. 13284 - 13297]