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12.3.1.4.1.7 Method 7: Use of “Betmip”; Reaction of Iminophosphoranes with α-Diketones

DOI: 10.1055/sos-SD-012-00398

Grimmett, M. R.Science of Synthesis, (200212360.

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]

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