TY - JOUR
T1 - 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
AU - Qiu, Yun
AU - Dlugosch, Michael
AU - Liu, Xin
AU - Khan, Faiyaz
AU - Ward, Jas S.
AU - Lan, Ping
AU - Banwell, Martin G.
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/10/5
Y1 - 2018/10/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85053834758&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01940
DO - 10.1021/acs.joc.8b01940
M3 - Article
SN - 0022-3263
VL - 83
SP - 12023
EP - 12033
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -