A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2-d] pyrimidines from pi-Deficient 1,2-Dihaloarenes and Geminal Enediamines

作者：Mishina Maria S; Ivanov Alexander Yu; Lobanov Pavel S; Dar' in Dmitrii V

来源：Synthesis (Germany), 2016, 48(17): 2851-2862.

DOI：10.1055/s-0035-1561645

• 2-aminoindoles
• pyrrolo[3,2-d]pyrimidines
• geminal enediamines
• cyclization
• copper catalyst
• N-arylation

An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and p-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.

• 出版日期2016-9