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Org Lett. 2006 Oct 12;8(21):4747-50. doi: 10.1021/ol061827m.

From bifunctional nucleophilic behavior of DBU to a new heterocyclic fluorescent platform.

Organic letters

Daniel T Gryko, Joanna Piechowska, Mariusz Tasior, Jacek Waluk, Grazyna Orzanowska

Affiliations

  1. Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. [email protected]

PMID: 17020293 DOI: 10.1021/ol061827m

Abstract

[structure: see text] An unexpected discovery of a novel cyclocondensation reaction of 1,8-diazabicyclo[5.4.0]undec-8-ene (DBU) with activated 1,2-dichloro compounds is described. The 2-aminopyrrole skeleton is generated through the concomitant formation of new nitrogen-carbon and carbon-carbon bonds. A new pentacyclic derivative formed upon the reaction of 2,3-dichloroquinoxaline with DBU exhibits strong fluorescence both in solutions (Phi in hexane = 0.4) and in the solid state.

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