155405-64-4Relevant academic research and scientific papers
A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines
Mishina, Maria S.,Ivanov, Alexander Yu.,Lobanov, Pavel S.,Dar'In, Dmitrii V.
, p. 2851 - 2862 (2016/08/30)
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.
Synthesis of 5H-pyrido[2,3-c]-2-benzazepines
Troschutz,Grun
, p. 225 - 231 (2007/10/02)
The title compounds can be obtained by two different ways: Ring closure of 2-benzazepine enaminonitrile 1 and the C2-building blocks 2, 7 and 8 gives rise to the title compounds 6, 9 and 10. - The second way starts with Wolff-Kishner-reduction of the 2-amino-3-benzoylpyridines 16a,b to the 2-amino-3-benzylpyridines 18a,b. Benzoylation of 18a,b leads to the dibenzoylated compounds 20 and 21, respectively, which can be transformed to the monobenzoylated pyridines 22 resp. 23. Applying the Bischler-Napieralski-reaction on 22a,b and 23a,b leads to the 5H-pyrido[2,3-c]-2-benzazepines 24a,b and 25a,b. By means of 1H-, 13C- and 15N-NMR-data it is demonstrated that ethyl benzoylcyanacetimidate (12a) exists as benzoylketene-O,N-acetal 12a AE.
