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Synthesis 2014; 46(10): 1413-1420
DOI: 10.1055/s-0033-1340902
DOI: 10.1055/s-0033-1340902
paper
Regioselective Synthesis of Dihydropyridocoumarin and Phenanthrolinone Derivatives via Iron(III) Chloride Mediated Intramolecular Cyclization
Further Information
Publication History
Received: 17 December 2013
Accepted after revision: 13 February 2014
Publication Date:
24 March 2014 (online)
Abstract
Potentially bioactive angular dihydropyridocoumarin and phenanthrolinone derivatives are synthesized in good to excellent yields using readily available iron(III) chloride (FeCl3) as the catalyst. The process is very simple, straightforward and inexpensive, and provides a diverse range of pyranoquinolone or phenanthrolinone derivatives, via a 6-endo-dig mode of cyclization, starting from simple and easily available 6-(N-propargyl)aminocoumarin and -quinolone derivatives.
Key words
pyranoquinolone - phenanthrolinone - iron(III) chloride - Sonogashira coupling - 6-endo-dig cyclizationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For some applications of the Sonogashira reaction in the synthesis of natural products, see:
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