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

doi:10.1016/j.tetlet.2011.03.065

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 journal › Article › peer-review

5 Scopus citations

Abstract

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 language	English
Pages (from-to)	2667-2669
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.065
State	Published - 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.

Keywords

Azomethine ylide
Nicotine analog synthesis
[3+2] Cycloaddition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.03.065

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@article{abbbd74b6ba747caaa40f44ec71abdb3,

title = "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",

abstract = "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.",

keywords = "Azomethine ylide, Nicotine analog synthesis, [3+2] Cycloaddition",

author = "Zhenfa Zhang and Dwoskin, {Linda P.} and Crooks, {Peter A.}",

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. ",

year = "2011",

month = may,

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doi = "10.1016/j.tetlet.2011.03.065",

language = "English",

volume = "52",

pages = "2667--2669",

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T1 - 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

AU - Zhang, Zhenfa

AU - Dwoskin, Linda P.

AU - Crooks, Peter A.

N1 - 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.

PY - 2011/5/25

Y1 - 2011/5/25

N2 - 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.

AB - 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.

KW - Azomethine ylide

KW - Nicotine analog synthesis

KW - [3+2] Cycloaddition

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DO - 10.1016/j.tetlet.2011.03.065

M3 - Article

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ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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