Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl₃/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4 H-carbazol-4-ones and Related Heterocycles
Compounds such as 3, the product of a palladium-catalyzed Ullmann cross-coupling of o-iodonitrobenzene and 2-iodocyclohex-2-en-1-one, undergo complementary modes of reductive cyclization depending upon the conditions employed. Thus, on treatment with hydrogen in the presence of palladium on carbon, the tetrahydrocarbazole 4 is formed, while reaction of the same substrate (3) with TiCl3 in acetone affords the 1,2,3,9-tetrahydro-4H-carbazol-4-one 6.
|Collections||ANU Research Publications|
|Source:||Journal of Organic Chemistry|
|01_Qiu_Reductive_Cyclization_of_2018.pdf||1.19 MB||Adobe PDF||Request a copy|
Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.