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Photocycloaddition of Quinoxaline-2(1H)-thiones to Alkenes

✍ Scribed by Takehiko Nishio

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
386 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

A synthetically useful C-C bond formation involving the photochemical addition of quinoxaline-2( 1 H )thiones to alkenes is described. Irradiation of the quinoxaline-2(1H)-thiones 1 4 in the presence of the alkenes 7 gave the 2-(2'-mercaptoalkyl)quinoxalines 8 1 1 in moderate-to-good yields via ring cleavage of an intermediate aminothietane with aromatization of the quinoxaline ring. The latter was formed by [2 + 21 photocycloaddition of the C=S bond of the quinoxaline-2(1H)-thione and the C=C bond of the alkene. ') Quite recently, we succeeded in the first isolation, though in low yield, of an aminothietane derived from the photochemical [2 + 21 cycloaddition of 1,3,3-trirnethyl-lH-indole-2(3H)-thione with 2-methylprop-1-ene Part of this work was reported in preliminary form [8].

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