Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides: A Bu3P-Mediated C-Acylation/Cyclization Sequence

Chia Jui Lee, Cheng Che Tsai, Shao Hao Hong, Geng Hua Chang, Mei Chun Yang, Lennart Möhlmann, Wen-Wei Lin

Research output: Contribution to journal › Article

23 Citations (Scopus)

Abstract

A Bu3P-mediated cyclization reaction of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones though electrophilic addition of acyl chlorides towards the synthesis of highly functionalized furo[3,2-c]coumarins bearing a phosphorus ylide moiety is described. These unprecedented cyclization reaction proceeds under mild reaction conditions within short reaction times (1 min to 1 h), and can be further applied in the synthesis of alkenyl-substituted furo[3,2-c]coumarins by the treatment with carbonyl electrophiles under basic conditions.

Original languageEnglish
Pages (from-to)8502-8505
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number29
DOIs
Publication statusPublished - 2015 Jul 13

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Coumarins
Acylation
Cyclization
Chlorides
Bearings (structural)
Phosphorus

Keywords

  • acylation
  • cyclizations
  • heterocycles
  • ylides
  • zwitterion

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides : A Bu3P-Mediated C-Acylation/Cyclization Sequence. / Lee, Chia Jui; Tsai, Cheng Che; Hong, Shao Hao; Chang, Geng Hua; Yang, Mei Chun; Möhlmann, Lennart; Lin, Wen-Wei.

In: Angewandte Chemie - International Edition, Vol. 54, No. 29, 13.07.2015, p. 8502-8505.

Research output: Contribution to journal › Article

Lee, CJ, Tsai, CC, Hong, SH, Chang, GH, Yang, MC, Möhlmann, L & Lin, W-W 2015, 'Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides: A Bu3P-Mediated C-Acylation/Cyclization Sequence', Angewandte Chemie - International Edition, vol. 54, no. 29, pp. 8502-8505. https://doi.org/10.1002/anie.201502789
Lee CJ, Tsai CC, Hong SH, Chang GH, Yang MC, Möhlmann L et al. Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides: A Bu3P-Mediated C-Acylation/Cyclization Sequence. Angewandte Chemie - International Edition. 2015 Jul 13;54(29):8502-8505. https://doi.org/10.1002/anie.201502789
Lee, Chia Jui ; Tsai, Cheng Che ; Hong, Shao Hao ; Chang, Geng Hua ; Yang, Mei Chun ; Möhlmann, Lennart ; Lin, Wen-Wei. / Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides : A Bu3P-Mediated C-Acylation/Cyclization Sequence. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 29. pp. 8502-8505.
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