Journal
CHEMISTRYSELECT
Volume 4, Issue 9, Pages 2663-2667Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201803715
Keywords
1,3-indanedione; multicomponent reaction; piperidin-4-one; spiro[indene-2,7 '-isoquinoline]; tetrahydroisoquinoline
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Funding
- National Natural Science Foundation of China [21572196]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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The piperidine promoted three-component reaction of N-alkylpiperidin-4-ones, malononitrile and 2-arylidene-1,3-indanediones in ethanol selectively resulted in the spiro[indene-2,7'-isoquinoline] and the ring-opened cis- or trans-1,2,8,8a-tetrahydroisoquinoline derivatives at room temperature or at the elevated temperature. However, the four-component reaction N-alkylpiperidin-4-ones, malononitrile, aromatic aldehydes and 1,3-indanedione in refluxing ethanol mainly afforded ring-opened cis-1,2,8,8a-tetrahydroisoquinoline derivatives in good yields and with high diastereoselectivity. A plausible domino reaction mechanism was proposed for the formation of the different polycyclic products.
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