Unprecedented 1,3-dipolar cycloaddition: from 1,4,5,8-naphthalene bisimides to a new heterocyclic skeleton

Daniel T Gryko; Maciej K Rogacki; Jan Klajn; Michał Gałezowski; Dorota K Stepień; Michał K Cyrański

doi:10.1021/ol1005032

Unprecedented 1,3-dipolar cycloaddition: from 1,4,5,8-naphthalene bisimides to a new heterocyclic skeleton

Org Lett. 2010 May 7;12(9):2020-3. doi: 10.1021/ol1005032.

Authors

Daniel T Gryko¹, Maciej K Rogacki, Jan Klajn, Michał Gałezowski, Dorota K Stepień, Michał K Cyrański

Affiliation

¹ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. daniel@icho.edu.pl

PMID: 20387891
DOI: 10.1021/ol1005032

Abstract

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.