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

Jiang-Sheng Li; Yuan Xue; Zhi-Wei Li; Wei-Dong Liu; Cui-Hong Lu; Pei-Xia Zhao

doi:10.1055/s-0033-1339501

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(15): 2003-2005
DOI: 10.1055/s-0033-1339501

letter

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

Jiang-Sheng Li*

^aHunan 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: jslichem@gmail.com eMail: lizwhn@126.com

,

Yuan Xue

^aHunan 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: jslichem@gmail.com eMail: lizwhn@126.com

,

Zhi-Wei Li*

^aHunan 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: jslichem@gmail.com eMail: lizwhn@126.com

,

Wei-Dong Liu

^bNational Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, P. R. of China

,

Cui-Hong Lu

^aHunan 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: jslichem@gmail.com eMail: lizwhn@126.com

,

Pei-Xia Zhao

^aHunan 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: jslichem@gmail.com eMail: lizwhn@126.com

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Abstract

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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.

Key words

furans - cyano ketones - DDQ - cyclization - fluorescent cores

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Referenzen

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.

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