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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-4H-carbazol-4-ones and Related Heterocycles

Author:
Qiu, Yun, Dlugosch, Michael, Liu, Xin, Khan, Faiyaz, Ward, Jas S., Lan, Ping, Banwell, Martin G.
Source:
Journal of organic chemistry 2018 v.83 no.19 pp. 12023-12033
ISSN:
1520-6904
Subject:
acetone, aldehydes, carbon, chemical structure, cross-coupling reactions, hydrochloric acid, hydrogen, iron, organic chemistry, palladium
Abstract:
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.
Agid:
6151829