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