1. Synthesis of π-extended N-fused heteroacenes via regioselective Cadogan reaction.
- Author
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Gong, Peng, Li, Leijiao, Sun, Jingbo, Xue, Pengchong, and Lu, Ran
- Subjects
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ACENES , *CHEMICAL reactions , *CARBAZOLE , *SUBSTITUTION reactions , *CHEMICAL synthesis - Abstract
New indolocarbazole derivatives have been synthesized via Cadogan reaction. It has been found that the reductive cyclization of 3-(2-nitrophenyl)carbazoles prefers to take place on 4-position instead of 2-position in carbazole rings. Because electrophilic substitution was one of the main steps in Cadogan reaction and the Fukui function analysis for 9-methyl-3-(2-nitrophenyl)-9 H -carbazole revealed that more positive part of f − ( r ) function was localized at 4-position than at 2-position in carbazole, the 4-position was the favorite reactive site for the reductive cyclization. Such regioselective Cadogan reaction would be useful for the synthesis of π-extended N -fused heteroacenes with desired functionalities. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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