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ABSTRACT: The Dawson-type polyoxometalate (POM) [P(2)V(3)W(15)O(62)](9-) is a prototype for inclusion of carbonyls of amides, ureas, carbamates, and thiocarbamates into polyoxometallic structures. The carbonyl-inserted POMs catalyze the oxidation of sulfides. Chemoselectivity depends primarily on the proton content of the POM, but it is also influenced by the organic substituent.
Organic Letters 11/2011; 13(22):5990-3. · 5.86 Impact Factor
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ABSTRACT: 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 the Ugi-Smiles coupling.
The Journal of Organic Chemistry 08/2007; 72(15):5835-8. · 4.45 Impact Factor
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ABSTRACT: 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 were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.
The Journal of Organic Chemistry 06/2007; 72(11):4169-80. · 4.45 Impact Factor
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ABSTRACT: Herein, we wish to report a new three-component formation of heterocyclic scaffolds based on a one-pot process from simple phenols. The key step of this procedure involves an ortho-quinone methide formation from Mannich adducts under alkylative conditions. The transient o-quinone methide has been trapped in situ with indole and diketone using lithium perchlorate as catalyst. The interest of this procedure has been furthermore demonstrated by a new three-component aminobenzofuran formation from phenols, aldehydes and isocyanides.
Organic & Biomolecular Chemistry 10/2006; 4(18):3410-3. · 3.70 Impact Factor
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ABSTRACT: New heterocyclic scaffolds can be easily prepared by the coupling of heteroaromatic phenols (pyridines, pyrimidines) with carbonyl compounds, amines, and isocyanides. This transformation related to the Ugi reaction probably involves a Smiles rearrangement. The scope of this methodology is further extended by the successful use of heterocyclic thiols to form highly functionalized thioamides.
Organic Letters 09/2006; 8(18):4019-21. · 5.86 Impact Factor
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Angewandte Chemie International Edition 01/2006; 44(48):7961-4. · 13.45 Impact Factor
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Tetrahedron Letters 50(15):1741-1743. · 2.68 Impact Factor
