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- Title
Photo-induced molecular transformations. Part 123. One-step synthesis of 1 H-benz[ f]indole-4,9-diones by a new regioselective photoaddition of 2-amino-1,4-naphthoquinone with various alkenes and its application to one-step synthesis of kinamycin skeleton
- Authors
Kobayashi, Kazuhiro; Takeuchi, Hiroyasu; Seko, Shinzo; Suginome, Hiroshi
- Abstract
2,3-Dihydro-1 H-benz[ f]indole-4,9-diones are formed in one-step in 45-82% yields by an unprecedented [2+3]-type regioselective photoaddition of 2-amino-1,4-naphthoquinone with various electron-rich alkenes and the [2+3] adducts derived from ammonaphthoquinone with vinyl ethers and vinyl acetate to give 1 H-benz[ f]indole-4,9-diones including a benzindole-dione with a kinamycin skeleton in 33-72% yields. A probable pathway leading to the formation of the dihydroindole-dione involving air oxidation of an intermediary hydroquinone is proposed.
- Publication
Helvetica Chimica Acta, 1991, Vol 74, Issue 5, p1091
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19910740518