Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in a reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one and malononitrile

Jie-Jie Liu; Liang Cheng; Hong-Yan Huang; Feng Wei; Dong Wang; Li Liu

doi:10.1039/C7OB00904F

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in a reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one and malononitrile†

Jie-Jie Liu,^ab Liang Cheng,

*^abc Hong-Yan Huang,^ab Feng Wei,^ab Dong Wang^a and Li Liu*^ab

Author affiliations

* Corresponding authors

^a Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: chengl@iccas.ac.cn, lliu@iccas.ac.cn

^b Key Lab of Functional Molecular Engineering of Guangdong Province (South China University of Technology), Guangzhou 510640, China

^c University of Chinese Academy of Sciences, Beijing 100049, China

Abstract

Chromone skeletons are widespread among natural products as well as bioactive molecules. Here, we describe an unprecedented reaction of furo[3,4-b]chromen-9-one with malononitrile to afford 3-(tetrahydrofuran-2-yl)-4H-chromen-4-ones. Experimental data suggest that a sequence of Michael/retro-Michael/nucleophilic addition is involved in this unprecedented transformation.

Download options Please wait...

Associated articles

Correction: Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one…

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7OB00904F
Article type: Paper
Submitted: 11 Apr 2017
Accepted: 25 May 2017
First published: 25 May 2017

Download Citation

Org. Biomol. Chem., 2017,15, 5078-5088

Permissions

Request permissions

Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in a reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one and malononitrile

J. Liu, L. Cheng, H. Huang, F. Wei, D. Wang and L. Liu, Org. Biomol. Chem., 2017, 15, 5078 DOI: 10.1039/C7OB00904F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in a reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one and malononitrile†

Abstract

Associated articles

Supplementary files

Article information

Download Citation

Permissions

Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in a reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one and malononitrile

Social activity

Search articles by author

Spotlight

Advertisements