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One‐Pot Three‐Step Synthesis of Naphtho[2,3‐ a ]carbazole‐ 5,13‐diones using a Tandem Radical Alkylation–Cyclization– Aromatization Reaction Sequence
Author(s) -
Ding Chunyong,
Tu Shanghui,
Yao Qizheng,
Li Fulong,
Wang Yuanxiang,
Hu Wenxiang,
Zhang Ao
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900789
Subject(s) - chemistry , aromatization , ammonium persulfate , tandem , alkylation , persulfate , carbazole , ammonium acetate , combinatorial chemistry , organic chemistry , nucleophile , decarboxylation , catalysis , radical cyclization , materials science , high performance liquid chromatography , composite material , polymerization , polymer
A three‐step, one‐pot tandem reaction including radical nucleophilic alkylation/cyclization/aromatization was developed using 0.3 equivalents of silver(I) acetate (AgOAc) as the catalyst and 2 equivalents of ammonium persulfate [(NH 4 ) 2 S 2 O 8 ] as the oxidant. This strategy is highly efficient for the assembly of pentacyclic complex carbazoles from aryl‐fused bromobenzoquinones and indol‐3‐ylpropanoic acid acids in 52–72% overall yields (three steps). This new approach provides a significant improvement over the previously reported methods and would greatly facilitate analog library construction of pentacyclic complex carbazoles and benefit further biological evaluation of these compounds.