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Multi-component anion relay cascade of 1-acetylcyclopropanecarboxamides, aldehydes and acrylonitrile: access to biscyanoethylated furo[3,2-c]pyridinones.

Organic & biomolecular chemistry (2012-05-10)
Shaoxia Lin, Ying Wei, Fushun Liang, Baozhong Zhao, Yanling Liu, Pengjun Liu
ABSTRACT

A highly efficient multi-component anion relay cascade reaction based on 1-acetylcyclopropanecarboxamides, aldehydes and acrylonitrile has been developed, which provides strategically novel and atom-economic access to biologically important biscyanoethylated furo[3,2-c]pyridinones. In this one-pot transformation, up to five bonds (one C-N, one C-O and three C-C bonds) were constructed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Acrylonitrile, ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
Sigma-Aldrich
2-Hydroxypyridine, 97%
Sigma-Aldrich
Acrylonitrile, ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
Supelco
Acrylonitrile, analytical standard
Supelco
Acrylonitrile solution, certified reference material, 5000 μg/mL in methanol
Levetiracetam impurity C, European Pharmacopoeia (EP) Reference Standard