Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization
A convenient method to access 5H-benzo[b]carbazol-6-yl ketones via a sequential Cu-catalyzed Friedel-Crafts alkylation reaction of indoles with 2-(2-(alkynyl)benzylidene)malonates and iodine-promoted electrophilic cyclization followed by nucleophilic substitution and aromatization was developed. The products of the functional 5H-benzo[b]carbazol-6-yl ketones were obtained with up to 98% yield. This journal is the Partner Organisations 2014.
PdCl2-Catalyzed domino reactions of 2-Alkynylbenzaldehydes with Indoles: Synthesis of Fluorescent 5H-Benzo[b]carbazol-6-yl Ketones
(Chemical Equation Reprentation) Synthetic methods: A new, selective Pd-catalyzed domino reaction of 2- alkynylbenzaldehydes with indoles has been developed for the synthesis of 5H-benzo[b]carbazol-6-yl ketones. The isobenzopyrylium complex is trapped by indole at room temperature to give 3-(1H-isochromen-1-yl)-y1)-indoles, which can be transformed into 5Hbenzo[b]carbazol-6-yl ketones by raising the temperature (see scheme). These ketones exhibit intense fluorescence and interact with metal ions to enhance the fluorescence intensity.
Tang, Ri-Yuan,Li, Jin-Heng
supporting information; experimental part
p. 4733 - 4738
(2010/07/05)
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