期刊
TETRAHEDRON LETTERS
卷 128, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2023.154682
关键词
4-Pyrones; Ketene dithioacetals; Soft Enolization; Polyketides; Claisen condensation; Heterocyclization
The tandem acylation-heterocyclization of ketene dithioacetals was performed using soft enolization in the MgBr2·OEt2/NEt3 system. A series of 3,6-substituted 2-methylthio-4-pyrones were obtained with a wide functional group tolerance. The obtained 2-methylthio-4-pyrones were demonstrated to undergo transformations, including substitution of the SMe group with N-nucleophiles, for the preparation of functionalized 4-pyrones as analogs of bioactive molecules.
The tandem acylation-heterocyclization of ketene dithioacetals was performed via soft enolization in MgBr2 center dot OEt2/NEt3 system. A series of 3,6-substituted 2-methylthio-4-pyrones were obtained with a wide functional group tolerance. The reaction showed a good scalability, and the isolation of the products was performed by crystallization without the use of chromatography. Some transformations of the obtained 2-methylthio-4-pyrones, including substitution of the SMe group with N-nucleophiles, have been demonstrated for the preparation of functionalized 4-pyrones as analogs of several bioactive molecules.
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