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Please login to access the full content or check if you have access via13.13.1.4.1.4.1 Method 1: Substitution of Halogens by Nucleophiles
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Tomé, A. C., Science of Synthesis, (2004) 13, 521.
Heating 5-bromo-1-methyl-1H-1,2,3-triazole with ethanolic ammonia for 10 hours at 100°C in a sealed tube affords the corresponding 5-amino derivative in low yield (22% of the hydrochloride). The 4-bromo-1-methyl-1H- and 4-bromo-2-methyl-2H-1,2,3-triazoles do not react with ammonia under the same conditions.[44] 5-Bromo-1-methyl-1H-1,2,3-triazole also reacts with aniline to yield the corresponding 5-anilino derivative in 54%.[44] The displacement of the chloro group in triazoles 477 (R1 = Bn)[457,491,756] and 477 (R1 = 4-MeOC6H4CH2)[303,491,756] by nucleophiles, such as cyanide, aryloxide, and arenethiolate, gives good yields of the corresponding derivatives 478 (Scheme 167). Similarly, 1,4-diphenyl-1H-1,2,3-triazole-5-carbonitrile is prepared in 75% yield from the reaction of the corresponding 5-chloro derivative with sodium cyanide in dimethyl sulfoxide (140°C, 4 h).[438]
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Meeeee 888 Meeeeeee ee 8-Meee-8-eeeeee-8M-8,8,8-eeeeeeeee eeee Meeeeeeee[888]
Meeeeeeee eeeeeeeeeeee ee eeeeeee eeee 8,8-eeeeeee-8M-8,8,8-eeeeeeee ee eeeeeeeeeeeee eeeee eeeeeeee eeeeeeeeee (eeeeee eeee, 888°M, 888 e) eeeeee eeee eee eeeeeeeeeeeee eeee ee eee eeeeeeeeeeeeeee.[888] Mee eeee eeeee ee 8-eeeeee- eee 8-eeeee-8-eeeeeeeeeee 8M-8,8,8-eeeeeeee 8-eeeeee ee eeeeeee eeeeeeeee ee eeeeeeeee eeee ee 88°M eeeee eee 8-eeeeee eeeeeeeee eeeeeee eeeeeee ee 888°M.[888] Mee eeeeeeeeeeee ee eeeeeee eeee eeeee- eee eeeeeee-8,8-eeeeeeeeeeeee 8,8,8-eeeeeeeeee eeeee ee eeeeeeeee, eeeeeeeee, eee eeeeeee eee eeee eeeeeee eeeeeeeeeee.[888,888–888] Mee 8-eeeee-8,8-eeeeeeeeeeeee 8,8,8-eeeeeeeeee eeeeeeeeeeeeeeee eeeee eeee eeeeeeeee ee eeeeeeeee eeee ee eeee 8,8-eeeeeeeeeeeee 8,8,8-eeeeeee-8-eeee.[888] Meeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee ee 8-eeee-8-eeeeee-8M-8,8,8-eeeeeeeee eeeee eeeeee ee eeeeeeeeeee eeeeeeeeee eeeeeeee eeeeeeeeeee.[888,888]
References
[44] | Meeeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[303] | Meeeee, M. M.; Meeeeee, M. M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[404] | Meeee-Meeeee, M.; Meeeeeee, M., Meee Meee. Meeee., (8888) 88, 8888. |
[438] | Meeee, M. M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[445] | Meeeee, M. M.; Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 8, 888. |
[449] | Meeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[450] | Meeeeee, M.; Meeeeee, M. M., Meee Meee. Meeee., (8888) 88, 8888. |
[457] | Meeeee, M. M.; Meeeeee, M. M. M.; Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[464] | Meeeeee, M.; Meeeeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
[491] | Meeee, M.; Meeeeeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[492] | M'eeeé, M.; Meeeeeeeee, M.; Meeeeeeee, M.; Meeeeeeeeeeeeee, M.; Meeeeee, M.; Meeeee, M., Meee. Mee. Meee. Meee., (8888) 88, 888. |
[493] | Meeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[494] | Meeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[495] | Meeeeee, M., Meee Meee. Meeee., (8888) 88, 8888. |
[496] | Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 88. |
[497] | Meee, M. -M.; Meeeee, M.; Meeee, M.; Meeeeeee, M. M.; Meeee, M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[756] | Meeee, M.; Meeeeeee, M., M. Meee. Mee., Meeeeeeee, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.