4.8 Article

Unprecedented 1,3-Dipolar Cycloaddition: From 1,4,5,8-Naphthalene Bisimides to a New Heterocyclic Skeleton

Journal

ORGANIC LETTERS
Volume 12, Issue 9, Pages 2020-2023

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1005032

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Funding

  1. Polish Ministry of Science and Higher Education [T09A 50612]

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1,4,5,8-Naphthalene bisimides react as dipolarophiles with in situ formed azomethine ylides. Double 1,3-dipolar cycloaddition is followed by unique ring rearrangement and leads to the formation of two six-membered rings. The formation of hexacyclic products is rationalized based on DFT calculations.

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