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Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins. | LitMetric

Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins.

Beilstein J Org Chem

Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow-226 001, India, , Tel: +91-(522)-2612 411, Extn: 4379.

Published: February 2013

Cu-catalyzed A(3) coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566765PMC
http://dx.doi.org/10.3762/bjoc.9.21DOI Listing

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