Efficient synthesis of N-alkyl-2,7-dihalocarbazoles by simultaneous carbazole ring closure and N-alkylation

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• 作者：Drahomí ; r Vý ; prachtický ; ; ^{vyprach@imc.cas.cz} ; Ivan Kmí ; nek ; Veronika Pokorná ; V¨§ra Cimrová ; ; ^{cimrova@imc.cas.cz}
• 关键词：Carbazole ring closure ; Carbazole alkylation ; Heterocycles ; Aromatic substitution ; Conjugated polymers
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：24 June, 2012
• 年：2012
• 卷：68
• 期：25
• 页码：5075-5080
• 全文大小：498 K

文摘

The N-alkyl-2,7-dihalocarbazole as the main product was formed by the reaction of 4,4?dihalo-2-nitrobiphenyl with aromatic nitro compound and trialkyl phosphite. The presence and crucial role of aromatic nitro compound causes simultaneous carbazole ring closure and N-alkylation unlike the Cadogan ring closure where non-alkylated carbazole is formed as a main product. In addition, the mixture of aromatic nitro compound and trialkyl phosphite was found to be a possible N-alkylating agent for heterocycles, such as carbazole or indole.