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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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