A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones

Sundaram Suresh, Prakash Bhimrao Patil, Pao Hsing Yu, Chia Chi Fang, Yin Zhi Weng, Veerababurao Kavala, Ching Fa Yao*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives. (Figure presented.).

Original languageEnglish
Pages (from-to)4915-4925
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number21
DOIs
Publication statusPublished - 2021 Nov 9

Keywords

  • 3-bromopropenals
  • One-pot synthesis
  • anilines
  • dimethyl sulfoxide
  • α-bromo enaminones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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