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; Wenwei Lin

doi:10.1002/anie.201502789

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, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

41 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 language	English
Pages (from-to)	8502-8505
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	29
DOIs	https://doi.org/10.1002/anie.201502789
Publication status	Published - 2015 Jul 13

Keywords

acylation
cyclizations
heterocycles
ylides
zwitterion

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201502789

Cite this

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title = "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",

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.",

keywords = "acylation, cyclizations, heterocycles, ylides, zwitterion",

author = "Lee, {Chia Jui} and Tsai, {Cheng Che} and Hong, {Shao Hao} and Chang, {Geng Hua} and Yang, {Mei Chun} and Lennart M{\"o}hlmann and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = jul,

day = "13",

doi = "10.1002/anie.201502789",

language = "English",

volume = "54",

pages = "8502--8505",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

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T1 - Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides

T2 - A Bu3P-Mediated C-Acylation/Cyclization Sequence

AU - Lee, Chia Jui

AU - Tsai, Cheng Che

AU - Hong, Shao Hao

AU - Chang, Geng Hua

AU - Yang, Mei Chun

AU - Möhlmann, Lennart

AU - Lin, Wenwei

PY - 2015/7/13

Y1 - 2015/7/13

N2 - 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.

AB - 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.

KW - acylation

KW - cyclizations

KW - heterocycles

KW - ylides

KW - zwitterion

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U2 - 10.1002/anie.201502789

DO - 10.1002/anie.201502789

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

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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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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CCDC 1034256: Experimental Crystal Structure Determination

CCDC 1034255: Experimental Crystal Structure Determination

CCDC 1034356: Experimental Crystal Structure Determination

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1034256: Experimental Crystal Structure Determination

CCDC 1034255: Experimental Crystal Structure Determination

CCDC 1034356: Experimental Crystal Structure Determination

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