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

Shuguang Zhou, Shuang Feng Dong, Xin Zhang, Shen Yuan Zhang, Teck Peng Loh*, Jie Sheng Tian*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)100-105
Number of pages6
JournalOrganic Chemistry Frontiers
Volume11
Issue number1
DOIs
Publication statusPublished - Nov 14 2023
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2024 The Royal Society of Chemistry

ASJC Scopus Subject Areas

  • Organic Chemistry

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