Microbiological Transformations. Part 9.

Incubation of 1,2,6,7-tetrahydropyrido[3,2,1-i,j]quinolin-3(5H)-one with C. elegans resulted in oxidation at the C-7 benzylic position, whereas 1-methyl-1,2,6,7-tetrahydropyrido[3,2,1-i,j]quinolin-5(3H)-one gave products resulting from oxidation at both benzylic positions. cis- and trans-1-Hydroxy-3-methyl-1,2,6,7-tetrahydropyrido [3,2,1-i,j]quinolin-5(3H)-ones were produced on incubation of 5-methyl-1,2,6,7-tetrahydro-pyrido[3,2,1-i,j]quinolin-3(5H)-one with C. elegans, in addition to trans-1-hydroxy-5-methyl-l,2,6,7-tetrahydro-pyrido[3,2,1-i,j]quinolin-3(5H)-one. Incubation of 1,2,5,6-tetrahydropyrrolo[3,2,1-i,j]quinolin-4-one with C. elegans resulted in dehydrogenation to 1,2-dihydropyrrolo[3,2,1-i,j]quinolin-4-one. Incubation of 2,3,6,7-tetrahydropyrido[3,2,1-i,j]quinolin-1(5H)-one with C. elegans resulted in benzylic attack at C-7.