Journal of Organic Chemistry p. 929 - 931 (1985)
Update date:2022-08-04
Topics:
Bobowski, George
The N-methylation of 3,4,9,9a-tetrahydro-1,4-ethano-3,4a-(iminoethano)-4aH-carbazol-2(1H)-one (1) under Eschweiler-Clarke reaction conditions using excess formaldehyde gave 3,4,9,9a-tetrahydro-6,8,9,12-tetramethyl-1,4-ethano-3,4a-(iminoethano)-4aH-carbazol-2(1H)-one (1b).When an equivalent amount of formaldehyde was used, the main products were 3,4,9,9a-tetrahydro-12-methyl-1,4-ethano-3,4a-(iminoethano)-4aH-carbazol-2(1H)-one (1c) and 1,3,4,9a-tetrahydro-12-methyl-1,4-ethano-3,4a-(iminoethano)-4aH-carbazole-9(2H)-carboxaldehyde (1d).
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