Microbiological transformations, part 6. Microbiological transformations of acyl derivatives of indoline, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine with the fungus Cunninghamella elegans

Abstract

Incubation of N-benzoyl and N-(p-toluoyl)indoline with Cunninghamella elegans resulted in reductive cleavage with the formation of indoline and the corresponding benzyl alcohol. N-Acetylindoline underwent normal benzylic hydroxylation and open chain analogues of N-(p-toluoyl)indolines were hydroxylated at the aryl methyl group by C. elegans. The fungus effected benzylic oxidation at the 4-position in N-benzoyl-1,2,3,4-tetrahydroquinoline and in N-benzoyl-1,2,3,4-tetrahydroisoquinoline derivatives. N-(p-Toluoyl)-1,2,3,4-tetrahydroquinoline and N-(p-ethylbenzoyl)-1,2,3,4-tetrahy-droisoquinoline were, however, hydroxylated at the alternative 4′-benzylic position. Incubation of N-(p-toluoyl)-2,3,4,5-tetrahydro-1 H-1 -benzazepine with C. elegans gave 5-hydroxy-N-(p-toluoyl)-2,3,4,5-tetrahydro-1 H-1 -benzazepine