Photoinduced Reactions of 1-Acetylisatin with Phenylacetylenes
Organic Letters2000Vol. 2(17), pp. 2583–2586
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Abstract
[reaction: see text]Photoinduced reactions of 1-acetylisatin 1 with diphenylacetylenes 2a-2c afforded the corresponding 3-methylene-2-indolones 4a-4e and 5a-5e in 80-90% yields via a spirooxetene intermediate. Similar irradiation of 1 with phenylacetylene, on the other hand, resulted in efficient formation of two diastereoisomeric dispiro[3H-indole-3,2'-furan-3',3"-(3H)-indole]-2,5',2"(2H,5'H,2"H )triones 6 and 7 via a reaction sequence with initial formation of the spirooxetene intermediate. The regioselectivity in the photocycloaddition of 1 with phenylacetylene and the reaction mechanism for the formation of 6 and 7 are discussed.
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