Tetrahedron letters2022,Vol.994.DOI:10.1016/j.tetlet.2022.153816

Synthesis of functionalized gamma-lactams by a lewis acid catalyzed ketene formation/cyclization/claisen rearrangement sequence of 5,5-disubstituted Meldrum's acid

Han, Mei Shen, Mei -Hua Zhu, Chi -Fan Xu, Hua -Dong Lin, Xiao-Wan
Tetrahedron letters2022,Vol.994.DOI:10.1016/j.tetlet.2022.153816

Synthesis of functionalized gamma-lactams by a lewis acid catalyzed ketene formation/cyclization/claisen rearrangement sequence of 5,5-disubstituted Meldrum's acid

Han, Mei 1Shen, Mei -Hua 1Zhu, Chi -Fan 1Xu, Hua -Dong 1Lin, Xiao-Wan1
扫码查看

作者信息

  • 1. Changzhou Univ
  • 折叠

Abstract

A series of gamma-lactams were synthesized by intramolecular aza-claisen rearrangement of ketenes using Meldrum's acid as ketene precursor. Derivatives of Meldrum's acid with tertiary ammonia structure were used as raw material, and the reaction was catalyzed by Lewis acid at high-temperature conditions under microwave. Ketene formation by losing acetone and CO2, cyclization and claisen rearrangement occurred in sequence to form the gamma-lactams. (C) 2022 Elsevier Ltd. All rights reserved.

Key words

gamma-Lactam/Meldrum's acid/Claisen rearrangement/Ketene formation/C-H INSERTION/MICROBIAL METABOLITE/RING EXPANSION/BETA-LACTAMS/CYCLOADDITION/LACTACYSTIN/ROUTE

引用本文复制引用

出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
被引量1
参考文献量36
段落导航相关论文