You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via31.28.1.1 Method 1: Direct Introduction of Nitrogen Using Bases
Please login to access the full content or check if you have access via
Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1565.
A long-known method for the replacement of an aromatic C—H bond by an aromatic C—N bond is the Chichibabin reaction, where, for example, pyridine is transformed into pyridin-2-amine (1) (Scheme 1).[1]
Meeeee 8 Meeeeeeee ee Meeeeee-8-eeeee eeee Meeeeeee[8]
Mee Meeeeeeeeee eeeeeeee ee eeeeeee eeeeeee ee eeeeeeeee eeeeeeee M—M eeeee eeeee ee eeeeeeeeeeee eeeeeeeee.[8] Mee eeeee eeee ee eee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeeee, eee eee eeeeeeeee ee eeeeee eeee eeeeeee eeeeee. Meeeee eeeeeee eeee 88 ee 888% eeee eeee eeeeeeee. Meee eeee ee eeeeeeee eeeeee eeeeeeeeee eeee eeeeeeeeee eee eeeeeeeeeee; eee eeeeeee, eeeeeeee ee eeee eeeeeeeee ee eeeeeee. Me eee ee eee 8-eeeeeeeee ee eeeeeeeee, eee eeeeeeeeeee eee ee ee eeeeeeeee ee eeeeeeee eee eeeeeeee. Mee eee ee eeeeeeeeeee eeeeeeee eee eeee ee e eeeeeeeee eeeeee, eeee ee ee eee eeeeeeeee ee 8-eeeeeeeeeeeee-8-eeeee (8) (Meeeee 8).[8] Me eeee eee 8- eee 8-eeeeeeeee eee eeeeeeee, eee eeeee eeeee ee eeeeee eeee eee 8-eeeeeeee.[8] Me eeeeee eeeeeeeeeeee (888°M ee eeeeeeeeeeeeeee ee ee eeeeeee), eeee eee 8- eee 8-eeeeeeeee eee ee eeeeeeee ee eee eeee eeee.[8] Meeeee eeeee ee eeeee eeee ee eee eeee eeeeee eee eee eeeee eeee eeeeee eeeeeee ee eeee ee eeeeeee, eeeee eeeeee eeeee eeeeeeeee eeeeee eeeeee ee ee eeeeeeee ee eeeeeeeee ee eeeeee eeeee. Mee eeee ee eeeeeeee eeee ee 88% eeeee eeeeee. Meeeeee eeeeeeee eeee eeee eeeeeeee eee eeee eeeeeeee, eeee ee eeeeeeeeeeee (eeeeeee, eeeeee), eeeeeeeeeeeeeee, eeeeeeeeeeeeee, eee eeeeee eeeeeee.
Meeeee 8 Meeeeeeee ee 8-Meeeeeeeeeeee-8-eeeee eeee 8-Meeeeeeeeeeeee[8]
Meeeeee, eee eeeeeeeeeee ee eeeeeeee M—M eeeee eeee eeeee eeeeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeeee eeee ee eeeeeeeeeee. Meeeeeeeeeee eee eeeeee eeeeeeeeeeeee ee eeeeeee eeeee 88% ee 8-eeeee-M,M-eeeeeeeeeeeeeee (8) (Meeeee 8).[8]
Meeeee 8 Meeeeeeee ee 8-Meeee-M,M-eeeeeeeeeeeeeee eeee Meeeeeeeeeee eee Meeeee Meeeeeeeeeeee[8]
Mee eeeeeeee eee eeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeeeeee, eeee ee eee eee eeeeeeeee ee eeeeeeeeee ee eee eeeeeeeeeee eeeeee ee 8-eeeee-M-eeeeeeeeeeeeee. Me eeee eeee, eeeeeeeeeeee eee eeeeeee eeeee 8-eeeee-M-eeeeeeeeeeeee (8) eeee eeeeeeeeeeeeeeeeeee eeeeeeeee ee eeee ee eee eeee (Meeeee 8).[8,8]
Meeeee 8 Meeeeeeee ee 8-Meeee-M-eeeeeeeeeeeee eeee Meeeeeeeeeee eee Meeeeee[8,8]
Meee eeeeee eee eeeeee eeeeeeeee ee eee eeee eee ee eeeeeeee ee eeeeee eeeee eeee eeeeeeeee eeeeee eeeee ee ee eeeeeeeeeeeeee ee eee eeee ee eeeeeeee.[8]
Me ee eeee eeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeeeeee eeeee eeeee eeeeeeeeee, eeee ee ee eee eeeeeeeee ee 8-eeeeeeeeeeeeeee-8-eeeee (8) eeee 8-eeeeeeeeeeeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee 8-Meeeeeeeeeeeeee-8-eeeee eeee 8-Meeeeeeeeeeeeeee[88]
M eeeeeee eeeeeeeee eee eeee eeee ee eeeeeeeee eee eeeee eeeeee eeee 8,8-eeeeeeeeeeeeee ee eeee 8,8-eeeeeeeeeeeeee-8,8-eeeeeee (8) ee eeee eeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee 8,8-Meeeeeeeeeeeee-8,8-eeeeeee eeee 8,8-Meeeeeeeeeeeee[88]
M eeeeee eee eeeee eeeeeeeeee eeeeee eee eee eeeeee eeeeeeeeeeee ee ee eeeee eeeee eeee ee eeeeeeee eeeeee eeeee eeeee eeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeee eeeeeeee, eeeee ee eeeeeeeeeeee eeeeeeeeeee eeeeeee, eee eeeeeee eeee eeeeee eeeeeeeeee,[88] eee(MM) eeeeeeee,[88] ee eeeeeeee.[88] Meeeeeee eeeeee eee eee eeeeeeee eeeeeeeeeeeeee eeeee eeee 88 ee 88%, eeee ee ee eee eeeeeeeee ee 8-eeeee-8-eeeeeeee (8) eeee 8-eeeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee 8-Meeee-8-eeeeeeee eeee 8-Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeee-8-eeeee (8); Meeeeee Meeeeeeee:[8]
MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.
MeMM8 (888 e, 8 eee) (eeeeee eeee Me eee MM8) eee eeeeeee eeee eeeee eeeeeee (888 eM). 8-Meeeeeeeeeeeee (888 e, 8 eee) eee eeeee eee eee eeeeeee eee eeeeee ee 888–888°M eee 8 e, eeee ee 888–888°M eee ee eeeeeeeeee 8 e, eee eeeeeee ee eeeeee eee 8 e. Mee eeeeeee eee eeeeee ee 88°M eee eeeeee eeee eee. Mee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeee M8M (8 ×). Mee eeeeeee eeeeee, eeeeeeeee e eeeee eeee eee eeeeeeeeee eeee eeee eeeeeee eee M8M, eeee eeeeeeee eee eeeeeeeee eeee MMMe8. Mee MMMe8 eeeee eee eeeeee eeee eeee M8M, eee eeee eeeeeeee eeee eee eeeeee eeeee. Mee eeeeeee eeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeee eeeeeeeeeeee ee eeeeeee eeeeeeee; eeeee: 888.8 e (88%); ee 88–88°M; ee 888–888°M/88 Meee.
References
| [1] | Meeeeeeeeee, M. M.; Meeee, M. M., Me. Meee. Mee.-Meee. M–ee., Meeee Meee., (8888) 88, 8888; Meee. Meeee., (8888) 8, 88888. |
| [2] | Meeeeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 88. |
| [3] | Meeeee, M. M.; Meeee, M., M. Me. Meee. Mee., (8888) 88, 88. |
| [4] | Meeeeeeeeee, M. M., Me. Meee. Mee.-Meee. M–ee., Meeee Meee., (8888) 88, 888; Meee. Meeee., (8888) 8, 88888. |
| [5] | Meeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeee, M.; Meeeeee, M. M., Mee. Mee. Meee., (8888) 88, 888. |
| [6] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 8, 88. |
| [7] | Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [8] | Meeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 888, 88888. |
| [9] | Me Meee, M. M., MM 88 888 888, (8888); Meee. Meeee., (8888) 888, 88888. |
| [10] | Meeeeeee, M., Mee. Meeee., (8888) 88, 88. |
| [11] | Meeeeeeeeeee, M.; Meeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
| [12] | Meeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [13] | Meeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
| [14] | Meeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [15] | Meeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 88. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 88.
Return to Top