New strategies for the synthesis of heteroannulated 2-pyridinones, substituted 2-quinolinones and coumarins from dehydroamino acid derivatives
| Autor: | Maria João R. P. Queiroz, Ricardo C. Calhelha, Ana S. Abreu, Paula M. T. Ferreira, M. Solange D. Carvalho |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Tandem 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Amino acid Acetic acid chemistry.chemical_compound Aniline chemistry Suzuki reaction Nucleophile Drug Discovery Organic chemistry Phenol |
| Zdroj: | Tetrahedron. 64:5139-5146 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2008.03.057 |
| Popis: | Several heteroannulated pyridinones were prepared from the methyl esters of N -Boc-β,β-diheteroaryldehydroalanines by treatment with acetic acid. The latter were obtained by a bis-Suzuki coupling of a β,β-dibromodehydroalanine with heteroarylboronate compounds. The products were obtained in good yields and the cyclization reaction involves the nucleophilic attack of one of the heteroaromatic rings on the carbonyl of the Boc group. The scope of this reaction was extended to the Z -isomer of N -Boc-β-heteroaryldehydrophenylalanines to give 4-phenylpyridinones. A tandem Suzuki coupling–cyclization protocol was developed for the synthesis of 2-quinolinones and coumarins. Thus, β-brominated dehydroamino acids were reacted with 2-(pinacolboronate)aniline or phenol in a one-pot Suzuki coupling followed by lactamization or lactonization to give the corresponding 3-amino-2-quinolinones or 3-aminocoumarins in good to high yields. This type of strategy was also applied to the synthesis of 2-quinolinones and coumarins linked in position-3 to amino acids, using as starting materials brominated dehydropeptides. |
| Databáze: | OpenAIRE |
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