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Photoinduced molecular transformations. Part 151. One-pot synthesis of 1H-benz[g]indole-4,5-diones by a regioselective (3+2) photoaddition of 4

✍ Scribed by Hiroshi Suginome; Hideo Sakurai; Akiyoshi Sasaki; Hiroyasu Takeuchi; Kazuhiro Kobayashi

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
578 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

1.5Fkm.@nMe+-di-dioaes ate formed in up to 82% yields by the (3+2) photoaddition d 4-b 1 &taphthoquinone with alkyl vinyl ethers in acetone with Pyrex-fdtered light, while a 1: 1 mixture of 23-dihydfo-lIf&e@glin&le~,5-di~ and23-~y~~[23-b9~~isfonncdin32%yieldbythe(3+2)photaadditiooofCamino-12-naphtboguimnewith isobutene in acetone. On the other hand, the irradiation of 4-phenylamino-1.2~naphthoquinone with alkenes. such as ethyl vinyl ether or isobutene, in acetone gave 23-dibydro4pheztyiimim~@tho[23-b~itrat-9-a1es, arising from the (3+2) photosiditioo in up to 34% yields. The intermediacy of the hydmqukm~ in these (3t2) pMoadditions was confii by tbe formation of acetates of the i-ate hydmqkones upon treating of the initial photoa&& with acetic aabydride.The formation me&a&m of these Q+2) photo&k& is discussed.

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