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Photoredox‐Catalyzed Isatin Reactions: Access to Dibenzo‐1,7‐Naphthyridine Carboxylate and Tryptanthrin
Author(s) -
Sultan Shaista,
Gupta Vivek,
Shah Bhahwal Ali
Publication year - 2017
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201700028
Subject(s) - isatin , umpolung , chemistry , photoredox catalysis , catalysis , decarbonylation , carboxylate , combinatorial chemistry , organic chemistry , nucleophile , photocatalysis
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.