Photoredox‐Catalyzed Isatin Reactions: Access to Dibenzo‐1, 7‐Naphthyridine Carboxylate and Tryptanthrin. Issue 4 (9th March 2017)

• Record Type: Journal Article
• Authors: Sultan, Shaista; Gupta, Vivek; Shah, Bhahwal Ali
• Is Part Of: ChemPhotoChem. Volume 1:Issue 4(2017)
• Page Start: 120
• Page End: 124
• Publication Date: 2017-03-09
• Subjects: isatins -- photocatalysis -- radical reactions -- tryptanthrin -- umpolung; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.201700028
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: A procedure for the synthesis of dibenzo‐1, 7‐naphthyridine carboxylate by means of photoredox catalysis has been developed. The reaction features an umpolung reaction of the keto group at the C‐3 position and entrapment of the decarbonylation‐prone C‐2 position of isatin. Additionally, the method is employed to showcase the chemodivergent behavior of isatins in aprotic solvents leading to the synthesis of tryptanthrin derivatives through photoredox catalysis. The reaction is demonstrated to be scalable (up to gram scale) and straightforward in terms of set up. Abstract : A fork in the road : Dibenzo‐1, 7‐naphthyridines and tryptanthrins have been prepared from isatins through photo‐redox catalysis employing a chemodivergent synthetic route. The different reactivities of isatins may possibly be attributed to the behavior of the ketyl radical of isatin in protic and aprotic solvents.