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2005
Photochemistry
O 0160
Intramolecular Photoreactions of Thiohomophthalimides with an Alkenyl Group
Their N-Side Chain. Regioselective Synthesis of Heterocycle-Fused Isoquino32- 055 in
line Derivatives Through [2 + 2] Photocycloaddition. — Within the dithiohomophthalimide series (I), the cycloaddition of an alkene moiety occurs regioselectively
at the aromatic thiocarbonyl in preference to the aliphatic thiocarbonyl yielding the
ring-fused isoquinolines (II). Dithiohomophthalimides (III) and (V) possessing a terminal styryl group in their side chain undergo a Norrish type II reaction. The tricyclic
ene-thiolactam compounds (VI) arise by elimination of hydrogen sulfide from the initially formed thiols. Isolable Paterno—Buechi products are not obtained. In the photoreaction of monothiohomophthalimides (VII) having an alkenyl substituent at the C-4
position, the cycloaddition of the alkene moiety occurs at the thiocarbonyl affording
two stereoisomers of bridged-ring compounds (VIII) and (IX). — (TAKECHI*, H.;
TAKAHASHI, H.; MACHIDA, M.; J. Heterocycl. Chem. 42 (2005) 2, 201-207; Fac.
Pharm. Sci., Health Sci. Univ. Hokkaido, Ishikari, Hokkaido 061, Japan; Eng.) —
H. Hoennerscheid
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