Photoinduced Molecular Transformations. Part 142. One??step syntheses of 1H??benz [f] indole??4, 9??diones and 1H??indole??4, 7??diones by a new regioselective …

K Kobayashi, H Takeuchi, S Seko, Y Kanno…

Index: Kobayashi; Takeuchi; Seko; Kanno; Kujime; Suginome Helvetica Chimica Acta, 1993 , vol. 76, # 8 p. 2942 - 2950

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Citation Number: 20

Abstract

Abstract The 2, 3-dihydro-1H-benz [f] indole-4, 9-diones 3a–d, h were formed in a one-step reaction in 13–82% yield by an unprecedented [3+ 2] regioselective photoaddition of 2- amino-1, 4-naphthoquinone (1) with various electronrich alkenes 2 (Scheme 1, Table). The [3+ 2] photoadducts derived from 1 with vinyl ethers and vinyl acetate gave 1H-benz [f] indole-4, 9-diones 4e, f, i, in 33–72% yield, by spontaneous loss of the corresponding ...