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Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational Strategy
Zolfigol, M.A. Khazaei, A. Karimitabar, F. Hamidi, M. Maleki, F. Aghabarari, B. Sefat, Farshid Mozafari, M.
Zolfigol, M.A.
Khazaei, A.
Karimitabar, F.
Hamidi, M.
Maleki, F.
Aghabarari, B.
Sefat, Farshid
Mozafari, M.
Publication Date
2018-04
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2017-12-03
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Abstract
Indolo[3,2-b]carbazole is a molecule of great biological significance, as it is formed in vivo after
consumption of cruciferous vegetables. The reaction of 1H-indole and various aldehydes in the presence
of a catalytic amount of N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
1,1-dioxide as an efficient and homogeneous catalyst in acetonitrile at 50°C produces 6,12-disubstituted
5,7-dihydroindolo[2,3-b]carbazole with an in good to excellent yield. The presented technique offers a fast
and robust method, by the use of inexpensive commercially available starting materials toward 6,12-
disubstituted 5,7-dihydroindolo[2,3-b]carbazole. A new anomeric-based oxidation was kept in mind for
the final step of the indolo[2,3-b]carbazoles synthesis. The suggested anomeric-based oxidation mechanism
was supported by experimental and theoretical evidences.
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Zolfigol MA, Khazaei A, Karimitabar F et al (2018) Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational Strategy. Journal of Heterocyclic Chemistry. 55(4): 1061-1068.
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