Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.
Bibliographical noteFunding Information:
We gratefully acknowledge financial support from the NIH ( Grant No. P41 GM076302 and P41 GM081267 ) and the University of Minnesota through the Vince and McKnight Endowed Chairs (to G.I.G).
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- Acetic anhydride
- Lithium perchlorate
- Multicomponent reaction