Beilstein J. Org. Chem.2021,17, 2765–2772, doi:10.3762/bjoc.17.186
. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5 in gram scale.
Keywords: 1-aminoisoquinolines; CWJ-a-5; intramolecular cyclisation; 2-(2-oxo-2-phenylethyl)benzonitriles; nucleophilic addition; Introduction
Heterocyclic compounds
-2-phenylethyl)benzonitriles with amines to deliver 1-aminoisoquinolines and its successful application in the synthesis of antitumor agent CWJ-a-5.
Results and Discussion
Initially we targeted the synthesis of 2-(2-oxo-2-phenylethyl)benzonitrile (3a) by reacting 2-methylbenzonitrile with the
found to be compatible with the present protocol delivering the corresponding 1-aminoisoquinolines (5v–x) in good yields (Scheme 4). The synthetic utility of this method was further extended towards the gram-scale synthesis of the antitumor agent CWJ-a-5. Accordingly, 2-(2-oxo-2-phenylethyl)benzonitrile
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Graphical Abstract
Figure 1:
Biologically active 1-aminoisoquinolines.