A reaction in its own right is the Ugi–Smiles reaction with the carboxylic acid component replaced by a phenol. In this reaction the Mumm rearrangement in the final step is replaced by the Smiles rearrangement .

Oct 19, 2014 · The Ugi–Smiles and Passerini–Smiles couplings are extensions of Ugi and Passerini reactions involving the use of acidic phenols in place of the traditional carboxylic acid partners. A Smiles rearrangement is in each case responsible for the final N …

This reaction, termed the phenol Ugi–Smiles system, leverages electron-deficient phenols to activate imines and induce irreversible rearrangements, resulting in the efficient formation of N-aryl amines. The reaction proceeds smoothly under mild conditions, yielding high amounts of the desired products.

Jun 22, 2007 · A new strategy involving Ugi-Smiles coupling followed by ring-closure metathesis is described herein for the preparation of pyrimidine-fused heterocyclic scaffolds. The scope of this sequence is presented in relation with the heteroatom effect observed in …

Jul 25, 2013 · Herein, focusing on the Ugi–Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results.

Apr 25, 2007 · The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields we...

Dec 1, 2014 · The Ugi–Smiles and Passerini–Smiles couplings are extensions of Ugi and Passerini reactions involving the use of acidic phenols in place of the traditional carboxylic acid partners. A Smiles rearrangement is in each case responsible for the final N …

Sep 22, 2010 · The four-component couplings of isocyanides with amines, aldehydes and phenols (Ugi–Smiles reactions) can be performed in water as the solvent instead of methanol or toluene.

Phenol Ugi–Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols

Oct 18, 2014 · The Ugi–Smiles couplings and Passerini–Smiles couplings of phenols and mercaptan offer new four-component access to N-aryl and O-aryl derivatives.