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Synthesis 2022; 54(07): 1765-1774
DOI: 10.1055/a-1628-5304
paper

Group-Assisted-Purification Chemistry Strategy for the Efficient Assembly of Cyclic Fused Pyridinones

Di Ke
a   College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China
,
You Wu
a   College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China
,
Lei Zhang
a   College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China
,
Jiaan Shao
b   School of Medicine, Zhejiang University City College, Hangzhou 310015, P. R. of China
,
Yongping Yu
a   College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China
,
Wenteng Chen∗
a   College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China
› Author AffiliationsThis project was supported by the Zhejiang Provincial Natural Science Foundation of China under Grant No. LD21H300001 to Y. Yu, and Zhejiang­ University special scientific research fund for COVID-19 prevention and control to W. Chen.
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Abstract

A group-assisted-purification (GAP) chemistry strategy-based Ugi four-center three-component reaction (Ugi-4C-3CR) was explored. The reaction proceeded well to deliver the cyclic fused pyridinones selectively. Moreover, the reaction conditions were mild and avoided additional chromatography or recrystallization workup. Also, wide variations in substrates, such as anilines and aliphatic amines as well as amino alcohols and amino acid esters were all tolerated and pyridinones are achieved in good to excellent yields. Importantly, ladder-type cyclic fused pyridinones can be further constructed in excellent yield of 91%.

Key words

group-assisted-purification (GAP) chemistry - cyclic fused pyridinones - gram-scale synthesis - high atom efficiency - good functional group tolerance

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1628-5304.
  • Supporting Information


Publication History

Received: 16 July 2021

Accepted after revision: 01 September 2021

Accepted Manuscript online:
01 September 2021

Article published online:
04 November 2021

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