Journal
TETRAHEDRON LETTERS
Volume 61, Issue 11-12, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.151606
Keywords
Spiropyrrolidine hybrid heterocycles; N-methylation; Eschweiler-Clarke reaction; NMR characterization
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Funding
- Deanship of Scientific Research at King Saud University [RG-1440-071]
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The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the decarboxylative condensation of acenaphthenequinone and tyrosine or phenylalanine to beta-nitrostyrenes afforded Spiro acenaphthylene-pyrrolidine hybrids. The subsequent reaction of these spiro heterocycles with formaldehyde and trifluoroacetic acid led to the formation of either Pictet-Spengler or Eschweiler-Clarke products depending on the substitution in the benzyl ring. The unsubstituted compounds occurred via Pictet-Spengler route to afford Spiro acenaphthylene pyrrolo[1,2-b]-soquinoline hybrids as expected, whereas the 4-OH substituted compounds proceeded via Eschweiler-Clarke route affording the unexpected N-methylated spiro acenaphthylene-pyrrolidine hybrids. (C) 2020 Elsevier Ltd. All rights reserved.
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