• Bulletin of the Korean Chemical Society
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• v.32 no.7
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• pp.2171-2177
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• 2011

Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzyl-idinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of $K_2CO_3$ and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).

• Journal of the Korean Chemical Society
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• v.42 no.2
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• pp.203-208
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• 1998

The photochemical reactivities of 2-halobenzyl phenyl ether, in which 2-halobenzyl moiety are tethered to phenyl moiety by the etheral alkyl linkage, has been studied. In the presence of nitrogen, the photochemical reaction of 2-chlorobenzyl phenyl ether (1) produces mainly phenol and photo-Fries type reaction products, while the corresponding bromo analog 2 produces photocyclization and photoreduced products, along with phenol and photo-Fries type products. The former result implies that since chlorine is bound to the benzyl ring firmly, the rather weaker $CH_{2}-O$ bond of 1 is cleavaged to produce the photo-Fries type product. The latter implies that the photoinduced fission of phenyl-bromine bond of 2 can compete with the fission of $CH_{2}-O$ bond, since the bond energy of phenyl-bromine is lower than that of phenyl-chlorine. Since by the presence of oxygen the formation of phenol is not affected much, the formation of photo-Fries type products is changed a little, and the formations of photocyclization and photoreduced products are affected effectively, a singlet state is involved in the formation of phenol, and both singlet and triplet state may be involved in the formation of photo-Fries type reaction, while a triplet state is involved in the formation of photocyclization and photoreduction products.