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( D , L )‐10‐Camphorsulfonic‐Acid‐Catalysed Synthesis of Diaryl‐Fused 2,8‐Dioxabicyclo[3.3.1]nonanes from 2‐Hydroxychalcones and Naphthol Derivatives
Author(s) -
Jiang Xiaolong,
Song Zilan,
Xu Chang,
Yao Qizheng,
Zhang Ao
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301295
Subject(s) - chemistry , toluene , aryl , friedel–crafts reaction , catalysis , stereochemistry , alkylation , medicinal chemistry , organic chemistry , alkyl
A tandem one‐pot Friedel–Crafts alkylation/double cyclization process to conveniently assemble diaryl‐fused 2,8‐dioxabicyclo[3.3.1]nonanes with aryl substituents at the C‐1 position was developed. 2‐Hydroxychalcones and naphthol derivatives reacted in refluxing toluene with ( D , L )‐10‐camphorsulfonic acid (CSA) as the catalyst. The transformation conveniently provided the corresponding 2,8‐dioxabicyclo[3.3.1]nonanes fused with one phenyl and one naphthyl group in moderate to good yields, and various substitutions on both reaction partners were tolerated. More importantly, aryl‐ and aza‐aryl‐fused 2,8‐dioxabicyclo[3.3.1]nonanes were prepared for the first time using this procedure.