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Photochemistry of di methyl quinoline 3 4 dicarboxylate n oxides

, : Photochemistry of di methyl quinoline 3 4 dicarboxylate n oxides. Australian Journal of Chemistry 36(7): 1419-1430

The photochemical rearrangement of 2-methyl and 2-aryl subsitituted dimethyl quinoline-3,4-dicarboxylate N-oxides was studied. In methanol or methanol/chloroform solutions the major product was the 1-methyl- or 1-aryl-quinolin-2(1H)-one in which the substituent at C2 has migrated to nitrogen. The yield of these products was increased in a dark reaction subsequent to the irradiation. In acetonitrile solutions the initial major product was the corresponding 3,1-benzoxazepine; subsequent reactions yielded inter alia indole derivatives. [This strain is related to the structure of perloline, a Lolium perenne alkaloid.].

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Horii, Z.; Kurihara, T.; Yamamoto, S.; Ninomiya, I., 1967: Studies on ergot alkaloids and related compounds. XIV. Synthesis of N-alkyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carboxamides and stereochemistry of diethyl 4-methyl-1-oxo-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-2,2-dicarboxylate. Chemical & Pharmaceutical Bulletin 15(11): 1641-1650

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