ReBr(CO)5-catalyzed sequential addition-cyclization of 1,3-dicarbonyl compounds with electron-deficient internal alkynes affording trisubstituted 2H-pyran-2-ones |
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Authors: | Wen-Guo Zhao |
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Institution: | Department of Chemistry, Tsinghua University, Innovative Catalysis Program, Key Laboratory of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Beijing 100084, China |
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Abstract: | The reaction of 1,3-dicarbonyl compounds such as acetoacetate, acetylacetone, dibenzoylmethane, and benzoylacetate with electron-deficient internal alkynes in the presence of catalytic amount of ReBr(CO)5 in toluene under neutral conditions resulted in the formation of 4,5,6-trisubstituted 2H-pyran-2-ones in moderate to high yield. The reaction took place via a two-step sequence including the rhenium(I)-catalyzed addition of the activated methylenes to alkynes to give enolic 2-alkenyl derivatives, and subsequently dealcoholic cyclization to form 2H-pyran-2-one derivatives. |
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Keywords: | 1 3-Dicarbonyl compounds Internal electron-deficient alkynes 2H-Pyran-2-ones Rhenium complexes |
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