Expeditious synthesis of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo- [3,2h]isoquinoline/[2,3-f]quinoline via azomethine ylide-alkene [3+2] cycloaddition

Zhenfa Zhang, Linda P. Dwoskin, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Expeditious syntheses of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo- [3,2h]isoquinoline/[2,3-f]quinoline have been developed. The syntheses started with commercially available materials and afforded excellent overall yields in straightforward steps. Intramolecular azomethine ylide-alkene [3+2] cycloaddition is the key step in the construction of these pyrroloisoquinoline and pyrroloquinoline scaffolds. This route is much more atom-economic than those reported in the literature and is appropriate for scale-up synthesis.

Original languageEnglish
Pages (from-to)2667-2669
Number of pages3
JournalTetrahedron Letters
Issue number21
StatePublished - May 25 2011

Bibliographical note

Funding Information:
This work was supported by a grant from the National Institutes of Health (U19DA017548, 2002-2007). We thank the University of Kentucky Mass Spectrometry Facility for providing high resolution mass spectral data for the compounds in this study.


  • Azomethine ylide
  • Nicotine analog synthesis
  • [3+2] Cycloaddition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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