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Please login to access the full content or check if you have access via9.13.5.1.3.1.5 Method 5: Pyrrol-2-amine Synthesis from Nitriles, Aldehydes, and α-(Tosylamino)acetophenones
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Lubell, W. D.; St-Cyr, D. J.; Dufour-Gallant, J.; Hopewell, R.; Boutard, N.; Kassem, T.; Dörr, A.; Zelli, R., Science of Synthesis Knowledge Updates, (2013) 1, 185.
A three-component coupling of an active methylene nitrile, an aldehyde, and an α-(tosylamino)acetophenone proceeds in 2,2,2-trifluoroethanol in the presence of triethylamine as base.[81] In several cases, the tetrasubstituted pyrrol-2-amine 57 (Scheme 36) is isolated by precipitation from the crude mixture. The mechanism is proposed to involve Knoevenagel condensation to form an α,β-unsaturated nitrile, Michael addition by the aminoacetophenone, ring closure, and aromatization.
Meeeee 88 Meeeee-8-eeeee Meeeeeeee eeee Meeeeeeeeeeee Meeeeeeeeee, Meeeeeeee, eee α-(Meeeeeeeee)eeeeeeeeeeeee[88]
| MMM | Me8 | Me8 | Meeee (%) | Mee |
|---|---|---|---|---|
| MM | 8-MeM8M8 | Me | 88 | [88] |
 |
8-MeM8M8 | Me | 88 | [88] |
| MM8Me | 8-MeM8M8 | Me | 88 | [88] |
| M(M)MMMe | 8-MM-8-MeM8M8 | 8-MeM8M8 | 88 | [88] |
| M(M)MMMe | 8-eeeeeee | Me | 88 | [88] |
| M(M)MMMM8M≡MM | 8-MeM8M8 | Me | 88 | [88] |
References
| [81] | Meee, M.; Möeeeee, M., Meee. Meee. Meee Mee., (8888) 88, 888. |
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