Silver-mediated synthesis of 1,4-dihydropyridine sulfones via [4 + 2] cyclization of N-allenylsulfonamides and enaminones with a 1,3-sulfonyl shift

Literature Information

Publication Date 2023-11-14
DOI 10.1039/D3QO01681A
Impact Factor 5.281
Authors

Shuguang Zhou, Shuang-Feng Dong, Xin Zhang, Shen-Yuan Zhang, Jie-Sheng Tian


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Abstract

This study outlines the development of an innovative tandem reaction involving [4 + 2] cyclization with 1,3-sulfonyl migration from N-allenylsulfonamides and enaminones, expanding the scope of synthetic methodologies for multifunctional 1,4-dihydropyridine derivatives. The outlined approach furnishes a broad spectrum of sulfonyl-substituted 1,4-dihydropyridine derivatives with good to excellent yields, which can be subsequently converted into diverse sulfonyl-substituted compounds such as pyridine, tetrahydropyridine, and piperidine derivatives through simplified operation. The methodological advancements achieved in this research not only demonstrate the versatility and applicability of the synthesized derivatives across varied substrates and conditions but also present promising potential for the development and diversification of unsymmetrical 1,4-dihydropyridine sulfones.

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Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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