You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via8.2.2.3 Method 3: Alkylation of Amines and Amides
Please login to access the full content or check if you have access via
Venturello, P.; Barbero, M., Science of Synthesis, (2006) 8, 900.
Regioselective N-alkylation of different heterocycles has been achieved using sodium hydride in the presence of various electrophiles. Methyl and ethyl indole-2-carboxylates,[14,15] heterocyclic ketene aminals,[16,17] 6-substituted pyridin-2-ones,[18] and optically active 4,5-dihydro-1,2,4-triazin-6(1H)-ones[19] have been alkylated using sodium hydride in dimethylformamide or 1,2-dimethoxyethane/dimethylformamide. Reaction of imidazolidine 16 with sodium hydride followed by bromoacetate gives alkylated products 17 (Table 1).
Meeee 8 Meeeeeeeee ee Meeeee eee Meeeee[88–88,88,88]
Meeeeeeee | Meeeeeeeee | Meeeeeeeee Meeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
MMM, 8°M ee ee | 88e | [88] | |||
MMM, ee | 88 | [88] | |||
MMM, 8–8°M | 88–88e | [88] | |||
MMM/MMM (8:8), 8°M | 88 | [88] | |||
MMM/MMM (8:8), 8°M | 88 | [88] | |||
MMM, 8–88°M | MeM | 88 | [88] |
e Meeee, eeeeeeeeee eeeeeee.
e Me8 = 8-MeM8M8; eeeee: 88%; Me8 = 8-Mee; eeeee: 88%.
Me eeeeeeeee eeeeee eee eee eeeee-eeeee eeeeeeeee ee eeeeeeeee eeee- eee eeeeeeeeeeeeeeee 88 eee eeee eeeeeeeee, eeeee eeee eeeeee eeeeeee ee e eeee ee eeeeeeeeeee eeeee-eeeee eeeeeeeeee 88 (Meeeee 8).[88]
Meeeee 8 Meeee-Meeee Meeeeeeee ee Meeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeee {8-[8-(8-Meee)-8-eeeeeeeeeeeee]eeeeeeeeeeee-8-ee}eeeeeeee 88; Meeeeee Meeeeeeee:[88]
Me 88% eeeeeeeeee ee MeM (8 eeee) ee eeeeeee eee eee eeeeee eeee eeeeeeeee eeeee eee eeee eeeee ee ee eee-eeeeee eeee ee 8-eeee-(8-eeeeeeeeeeee-8-eeeeeee)eeeeeeee 88 (8 eeee) ee eeeee MMM (88 eM) eeee eeeeeeee. Mee eeeeeee eee eeeeeee eeeee ee eeee M8 eee eeeeeee. Meee e eeee ee eeeee eeeeeeeeeeee (8 eeee) ee eeeee MMM (8 eM) eee eeeee eeeeeeee. Meeee eeeeeeee eee e eeeeeee 88 eee eee eeeeeee eee eeeeee eeee M8M (888 eM) eee eeeeeeeee eeee MM8Me8 (8 × 888 eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMe8) eee eee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeee eeee e eeeee eeeeee ee M8M eee eee eeeee eeeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeeeee eeeeeee; eeeee: 88–88%.
Meeeeeeeee 88; Meeeeee Meeeeeeee:[88]
Mee eeeeeeeeeeeeee eeeee 88 (88 ee, 8.888 eeee) eee 88% MeM (8.8 ee, 8.88 eeee) ee eeeeeee eee eeee eeeeee ee MMM (8.8 eM) eee 8.8 e. Mee eeeeeeeeee eeeee (8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeee ee 88°M eee 88 e. Mee eeeee eee eeeeee eeeeeeeeeeee eeee MMM (8 × 8 eM), MeMM (8 × 8 eM), eee MM8Me8 (8 × 8 eM). Mee eeeeeee eeeee eee eeeeee eeee MMM/MM8Me8 (8:8) eee 8 eee, eeeeeeeee ee eeeeeeeeee, eeeeee, eee eee eeeeeee eee eeeeeee ee eeeee eeeeeeeee 88; eeeee: 88–88% (ee. 88% eeeeee).
References
[14] | Mee, M. M.; Meeee, M. M.; Meee, M. M.; Meeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[15] | Méeeee, M. M.; Meeeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
[16] | Meee, M.-M.; Me, M.-M.; Meeee, M.-M., Meeeeeeee, (8888), 8888. |
[17] | Meee, M.-M.; Me, M.-M.; Meeee, M.-M., Meeeeeeeee. Meeeee., (8888) 8, 888. |
[18] | Mee, M.; Me, M.-M.; Meeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[19] | Meeeèee, M.; Meeeeee, M.; Meeeeeeeeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 888. |
[20] | Meeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.