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10.13.1.1.1.3.2.4 Method 4: From o-(Benzoylamino)aryl Nitriles

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (2010281.

Treatment of o-(benzoylamino)aryl nitriles 305 with a 2-bromo ketone and cesium carbonate results, after hydrolysis of the benzoyl group, in the formation of 3-amino-2-acyl-1H-indoles 306 (Scheme 108).[‌292‌] This synthesis must involve firstly amide N-alkylation and then a base-promoted intramolecular nucleophilic attack on the nitrile, with subsequent tautomerization.

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