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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

42 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	8502-8505
頁數	4
期刊	Angewandte Chemie - International Edition
卷	54
發行號	29
DOIs	https://doi.org/10.1002/anie.201502789
出版狀態	已發佈 - 2015 7月 13

ASJC Scopus subject areas

催化
一般化學

存取文件

10.1002/anie.201502789

其它文件與鏈接

Link to publication in Scopus

CCDC 1034256: Experimental Crystal Structure Determination
Lee, C. (Creator), Tsai, C. (Creator), Hong, S. (Creator), Chang, G. (Creator), Yang, M. (Creator), Möhlmann, L. (Creator) & Lin, W. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc13q735, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13q735&sid=DataCite
資料集: Dataset
CCDC 1034255: Experimental Crystal Structure Determination
Lee, C. (Creator), Tsai, C. (Creator), Hong, S. (Creator), Chang, G. (Creator), Yang, M. (Creator), Möhlmann, L. (Creator) & Lin, W. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc13q724, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13q724&sid=DataCite
資料集: Dataset
CCDC 1034356: Experimental Crystal Structure Determination
Lee, C. (Creator), Tsai, C. (Creator), Hong, S. (Creator), Chang, G. (Creator), Yang, M. (Creator), Möhlmann, L. (Creator) & Lin, W. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc13qbbh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13qbbh&sid=DataCite
資料集: Dataset

引用此

@article{754b142eeae74fa0b34f8d4f38830334,

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",

number = "29",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84947865926&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84947865926&partnerID=8YFLogxK

U2 - 10.1002/anie.201502789

DO - 10.1002/anie.201502789

M3 - Article

C2 - 26033344

AN - SCOPUS:84947865926

SN - 1433-7851

VL - 54

SP - 8502

EP - 8505

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1034256: Experimental Crystal Structure Determination

CCDC 1034255: Experimental Crystal Structure Determination

CCDC 1034356: Experimental Crystal Structure Determination

引用此

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