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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 material 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 appropriate for scale-up synthesis.

SUBMITTER: Zhang Z

PROVIDER: S-EPMC3727292 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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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.

Zhang Zhenfa Z Dwoskin Linda P LP Crooks Peter A PA

Tetrahedron letters 20110501 21

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 material 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 thos ...[more]

PMID: 23908558

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