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Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational StrategyZolfigol, M.A., Khazaei, A., Karimitabar, F., Hamidi, M., Maleki, F., Aghabarari, B., Sefat, Farshid, Mozafari, M. 01 February 2018 (has links)
No / 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. / The Grant of Allameh Tabataba’i’s Award, Grant Number: BN093
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