Metal-free and benign approach for the synthesis of dihydro-5′H-spiro[benzo[c]chromene-8,4′-oxazole]-5′,6(7H)-dione scaffolds as masked amino acids
| Autor: | Behnaz Shafiee, Jackson O. Lay, Rohana Liyanage, Hadi Amiri Rudbari, Rudy Timm, M. Hassan Beyzavi, Joseph Duffield, Ahmad Reza Khosropour |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Decarboxylation 010402 general chemistry 01 natural sciences Pollution Medicinal chemistry 0104 chemical sciences Amino acid Solvent chemistry.chemical_compound Cascade reaction Atom economy Propylene carbonate Michael reaction Environmental Chemistry Oxazole |
| Zdroj: | Green Chemistry. 21:2656-2661 |
| ISSN: | 1463-9270 1463-9262 |
| Popis: | An eco-friendly, straightforward, and three-component condensation/cascade reaction of 4-hydroxycoumarins and (Z)-azlactones to construct diversified dihydro-5′H-spiro[benzo[c]chromene-8,4′-oxazole]-5′,6(7H)-diones as new masked amino acid derivatives has been developed with high to excellent yields and regio- and diastereoselectivity. This metal-free reaction proceeds via a one-pot cascade Michael addition/lactonization/decarboxylation reaction utilizing reusable propylene carbonate as a green solvent. The scale-up examination was also performed, showing high atom economy under the reaction conditions. Moreover, the mechanism of the reaction was further investigated using isotope-labeling, LC-MS monitoring, and TLC-MALDI-MS. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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