Chemo‑, Regio‑, and Stereoselective Construction of Core Skeleton of Furo[2,3‑b]pyrrole via Multicomponent Bicyclization Reaction

An efficient and straightforward N-ethyldiisopropylamine (DIPEA)-catalyzed multicomponent bicyclization reaction was developed to synthesize furo­[2,3-b]­pyrrole derivatives from β-ketothioamides, glyoxals, and ethyl cyanacetate in EtOH at rt for 1.5 h. This was achieved via a sequential Knoevenagel...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-06, Vol.82 (11), p.5566-5573
Main Authors: Man, Ning-Ning, Wang, Jia-Qi, Zhang, Li-Ming, Wen, Li-Rong, Li, Ming
Format: Article
Language:English
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Summary:An efficient and straightforward N-ethyldiisopropylamine (DIPEA)-catalyzed multicomponent bicyclization reaction was developed to synthesize furo­[2,3-b]­pyrrole derivatives from β-ketothioamides, glyoxals, and ethyl cyanacetate in EtOH at rt for 1.5 h. This was achieved via a sequential Knoevenagel condensation, Michael addition, and double cyclization, resulting in continuous formation of four chemical bonds (two C–C, two C–O, and one C–N bonds), two five-membered cycles, and three stereogenic centers in a one-pot operation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00371