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Photocycloaddition of Quinoxaline‐2(1 H )‐thiones to Alkenes
Author(s) -
Nishio Takehiko
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750208
Subject(s) - quinoxaline , chemistry , alkene , aromatization , ring (chemistry) , bond cleavage , medicinal chemistry , cleavage (geology) , photochemistry , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
A synthetically useful CC bond formation involving the photochemical addition of quinoxaline‐2(1 H )‐thiones to alkenes is described. Irradiation of the quinoxaline‐2(1 H )‐thiones 1–4 in the presence of the alkenes 7 gave the 2‐(2′‐mercaptoalkyl)quinoxalines 8–11 in moderate‐to‐good yields via ring cleavage of an intermediate aminothietane with aromatization of the quinoxaline ring. The latter was formed by [2+2] photocycloaddition of the CS bond of the quinoxaline‐2(1 H )‐thione and the CC bond of the alkene.