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Synthesis 2016; 48(17): 2851-2862
DOI: 10.1055/s-0035-1561645
DOI: 10.1055/s-0035-1561645
paper
A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2-d]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines
Further Information
Publication History
Received: 26 February 2016
Accepted after revision: 18 April 2016
Publication Date:
24 May 2016 (online)
Abstract
An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and π-deficient 1,2-dihaloarenes is presented. The two-step methodology includes aromatic nucleophilic substitution of the activated halogen of dihaloarene with enediamine C-nucleophilic center followed by Cu-catalyzed intramolecular N-arylation. This approach allows access to a variety of 2-amino-6-nitroindoles and 6-aminopyrrolo[3,2-d]pyrimidines (including N-mono- and N,N-disubstituted) in moderate and good yields under mild conditions.
Keywords
2-aminoindoles - pyrrolo[3,2-d]pyrimidines - geminal enediamines - cyclization - copper catalyst - N-arylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561645.
- Supporting Information
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For recent reviews on indole synthesis, see:
For reviews on indole-containing natural compounds, see:
For reviews on biologically active indole derivatives, see:
For reviews on geminal enediamines in heterocyclic synthesis, see: