Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3-carboxylates and 3-carbonitriles |
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| Authors: | Xingxian Gu Gunda I. Georg |
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| Affiliation: | 1. Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045, United States;2. Department of Medicinal Chemistry and Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street, SE, Minneapolis, MN 55414, United States |
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| Abstract: | 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. |
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| Keywords: | Multicomponent reaction Catalysis Lithium perchlorate Acetic anhydride Triphenylphosphine 2,5-Dioxooctahydroquinolines |
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