(D,L)-10-Camphorsulfonic-Acid-Catalysed Synthesis of Diaryl-Fused 2,8-Dioxabicyclo[3.3.1]nonanes from 2-Hydroxychalcones and Naphthol Derivatives

doi:10.1002/ejoc.201301295

	(D,L)-10-Camphorsulfonic-Acid-Catalysed Synthesis of Diaryl-Fused 2,8-Dioxabicyclo[3.3.1]nonanes from 2-Hydroxychalcones and Naphthol Derivatives
	Jiang, Xiaolong 1,2,3; Song, Zilan 2,3; Xu, Chang 1; Yao, Qizheng 1; Zhang, Ao2,3
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2014-01
期号	2 页码:418-425
关键词	Oxygen heterocycles Nitrogen heterocycles Cyclization Aromatic substitution Fused-ring systems Acid catalysis
ISSN号	1434-193X
DOI	10.1002/ejoc.201301295
文献子类	Article
英文摘要	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.
资助项目	Distinguished Young Scholars of the Chinese National Science Foundation (NSF)[81125021] ; Distinguished Young Scholars of the Chinese National Science Foundation (NSF)[81373277] ; National Science & Technology Major Project, Key New Drug Creation and Manufacturing Program, China[2012ZX09103-101-035] ; National Science & Technology Major Project, Key New Drug Creation and Manufacturing Program, China[2012ZX09301001-001] ; Interdisciplinary Cooperation Team, Program for Science and Technology Innovation (CAS)[00000000] ; State Key Laboratory of Drug Research[SIMM1302KF-08] ; Shanghai Institute of Materia Medica[00000000]
WOS关键词	FLAVYLIUM SALTS ; CONDENSATION PRODUCTS ; PROANTHOCYANIDINS ; PHENOLS ; ACID ; 4-HYDROXYCOUMARIN ; CONSTITUENTS ; TUBE
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000336266400018
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277288]
专题	药物化学研究室
通讯作者	Yao, Qizheng
作者单位	1.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China; 2.SIMM, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China; 3.SIMM, SOMCL, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Jiang, Xiaolong,Song, Zilan,Xu, Chang,et al. (D,L)-10-Camphorsulfonic-Acid-Catalysed Synthesis of Diaryl-Fused 2,8-Dioxabicyclo[3.3.1]nonanes from 2-Hydroxychalcones and Naphthol Derivatives[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014(2):418-425.
APA	Jiang, Xiaolong,Song, Zilan,Xu, Chang,Yao, Qizheng,&Zhang, Ao.(2014).(D,L)-10-Camphorsulfonic-Acid-Catalysed Synthesis of Diaryl-Fused 2,8-Dioxabicyclo[3.3.1]nonanes from 2-Hydroxychalcones and Naphthol Derivatives.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(2),418-425.
MLA	Jiang, Xiaolong,et al."(D,L)-10-Camphorsulfonic-Acid-Catalysed Synthesis of Diaryl-Fused 2,8-Dioxabicyclo[3.3.1]nonanes from 2-Hydroxychalcones and Naphthol Derivatives".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .2(2014):418-425.