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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

Qiu, Yun; Dlugosch, Michael; Liu, Xin; Khan, Faiyaz; Ward, Jas; Lan, Ping; Banwell, Martin


Compounds such as 3, the product of a palladium[0]-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.

CollectionsANU Research Publications
Date published: 2018
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.8b01940
Access Rights: Open Access


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