Synlett 2013; 24(15): 2003-2005
DOI: 10.1055/s-0033-1339501
letter
© Georg Thieme Verlag Stuttgart · New York

An Efficient Access to Fluorescent 2,3,4-Tricyanofurans from α-Cyano Ketones Using DDQ as Maleonitrile Building Block

Jiang-Sheng Li*
a  Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China   Fax: +86(731)85258733   Email: [email protected]   Email: [email protected]
,
Yuan Xue
a  Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China   Fax: +86(731)85258733   Email: [email protected]   Email: [email protected]
,
Zhi-Wei Li*
a  Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China   Fax: +86(731)85258733   Email: [email protected]   Email: [email protected]
,
Wei-Dong Liu
b  National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, P. R. of China
,
Cui-Hong Lu
a  Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China   Fax: +86(731)85258733   Email: [email protected]   Email: [email protected]
,
Pei-Xia Zhao
a  Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China   Fax: +86(731)85258733   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 28 May 2013

Accepted after revision: 11 July 2013

Publication Date:
14 August 2013 (online)


Abstract

An efficient synthetic method was developed for the synthesis of 2,3,4-tricyanofurans from α-cyano ketones using DDQ as maleonitrile building block under very mild conditions. This methodology allows for the construction of a new kind of fluorescent core framework.

Supporting Information

 
  • References and Notes

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  • 11 Experimental Procedure DDQ (341 mg, 1.5 mmol) was added to α-cyano ketone (0.5 mmol) in EtOAc (2 mL). The resulting reaction mixture was stirred overnight during which time a yellow solid precipitated. EtOAc (30 mL) was added, and the resultant mixture was subsequently washed with cold aq 5% NaHCO3 (3 × 10 mL) and brine. Silica gel (0.5 g) was added and the mixture rotary evaporated. The resulting powder was added to the top of a short silica gel column and purified using PE–EtOAc in a 10:1 to 7:1 ratio (v/v) as the eluent to afford the desired product.