Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

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

Chemo-, Regio-, and Stereoselective Construction of Core Skeleton of Furo[2,3-b]pyrrole via Multicomponent Bicyclization Reaction
Li-Ming Zhang, Jia-Qi Wang, Ning-Ning Man, Li-Rong Wen, Ming Li
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00371

DOI: 10.1021/acs.joc.7b00371

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