Journal
SYNTHESIS-STUTTGART
Volume -, Issue 2, Pages 239-248Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1217128
Keywords
coumarins; Michael addition; heterocycles; cyclizations; chromenes
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The reaction of various coumarins with cyanoacetamide derivatives under basic conditions (sodium ethoxide, piperidine or 2,2,6,6-tetramethylpiperidine), proceeds via an interesting process which involves skeletal rearrangement of the coumarin, a Michael addition and two cyclizations to afford 5-amino-1,10b-dihydro-2H-chromeno[3,4-c]pyridine-2,4(3H)-diones. The same reaction in the presence of N,N'-ethane-1,2-diylbis(2-cyanoacetamide) gives the corresponding mono and bis 5-amino-1,10b-dihydro-2H-chromeno[3,4-c]pyridine-2,4(3H)-diones.
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