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10.23.1.1.1.2.1.2.1 From (2-Nitrophenyl)acetonitrile and 4H-1-Benzopyran-4-ones

DOI: 10.1055/sos-SD-110-01096

Joule, J. A.Science of Synthesis Knowledge Updates, (2018212.

A comparable sequence can be employed using 4H-1-benzopyran-4-ones (chromones, e.g. 47) as the acceptor of the nucleophile, (2-nitrophenyl)acetonitrile (40), to furnish 2-(2-hydroxyaryl)-9H-pyrido[2,3-b]indoles 48 (Scheme 14).[‌50‌] It is significant that it is not necessary to postulate an oxidation step in this variant to rationalize the formation of products 48 and, doubtless as a consequence of this, the yields are much higher.

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