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Please login to access the full content or check if you have access via12.3.1.4.1.7 Method 7: Use of “Betmip”; Reaction of Iminophosphoranes with α-Diketones
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Grimmett, M. R., Science of Synthesis, (2002) 12, 360.
The reagent betmip (1-{[(triphenylphosphoranylidene)amino]methyl}-1H-benzotriazole, 68)[140] forms iminophosphoranes 69 on reaction with primary amines. These cyclize when treated with α-diketones to give 1,4,5-trisubstituted 1H-imidazoles 70, often in good yields (Scheme 39). With unsymmetrical α-diketones, the more nucleophilic iminophosphorane nitrogen atom becomes attached to the more-activated carbonyl carbon, giving rise to only one regioisomer.[141]
Meeeee 88 8,8,8-Meeeeeeeeeeeee Meeeeeeeee eeee Meeeeeeeeeeeeeeee eee α-Meeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeee-8,8-eeeeeeee-8M-eeeeeeeee (88, M8 = Meeeeeeeeee; Me8 = Me8 = Me); Meeeeee Meeeeeeee:[888]
Me e eeee ee 8-{[(eeeeeeeeeeeeeeeeeeeeeeeeee)eeeee]eeeeee}-8M-eeeeeeeeeeeee (88; 8.8 e, 8.8 eeee) ee MMM (888 eM) eee eeeee eeeeeeeeeeeeeeee (8.88 e, 8.8 eeee) eee eee eeeeeee eee eeeeee eeeee eeeeee eee 88 e eeeeee eeeeee eeeeee (8.8 e, 8.8 eeee) eee eeeeeeeee eeeee eee 88 e. Mee eeeeeee eee eeee eeeeee, eeeeeee eeee Me8M (888 eM), eee eeeeee eeee 8 M MMM (8 × 88 eM) ee eeeeee eee eeeeeeeeeeeee. Mee eeeee eeeeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M) ee eeeeee eeeeeeeeeeeeeeeeee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888.8°M.
References
[140] | Meeeeeeee, M. M.; Meeee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
[141] | Meeeeeeee, M. M.; Meeee, M.; Meeeee, M. M., Meeeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 88.