Poorly nucleophilic aromatic amines (nitroanilines, chloroanilines, etc.) react readily and selectively with trans-4-methoxy-3-buten-2-one, a convenient, effective and inexpensive surrogate for 3-butyn-2-one, to afford (Z)-enaminones. The efficiency of the reaction mostly lies in the use of water as a solvent, which enhances the reaction rate by a 45 to 200-fold factor with regard to other media.

The "on water" reaction of aromatic amines with 4-methoxy-3-buten-2-one is an efficient and cost-effective method for preparing (Z)-enaminones, with water as a solvent enhancing the reaction rate by 45 to 200-fold compared to other media.

Paper

"On water" reaction of deactivated anilines with 4-methoxy-3-buten-2-one, an effective butynone surrogate.

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