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 | Zendy

Yun Qiu | Zendy; Michael Dlugosch | Zendy; Xin Liu | Zendy; Faiyaz Khan | Zendy; Jas S. Ward | Zendy; Ping Lan | Zendy; Martin G. Banwell | Zendy

Open Access

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(s) -

Yun Qiu,

Michael Dlugosch,

Xin Liu,

Faiyaz Khan,

Jas S. Ward,

Ping Lan,

Martin G. Banwell

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b01940

Subject(s) - chemistry , palladium , acetone , medicinal chemistry , substrate (aquarium) , hydrogen , aldehyde , organic chemistry , catalysis , oceanography , geology

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 TiCl 3 in acetone affords the 1,2,3,9-tetrahydro-4 H-carbazol-4-one 6.

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