One-pot synthesis of 12H-benzo[b]xanthen-12-ones and naphtha[2,3-b]furans from non-naphthalene substrates

被引：3

作者：

He, Yan ^{[1
]}

Guo, Shenghai ^{[1
]}

Fan, Xuesen ^{[1
]}

Guo, Chenhao ^{[1
]}

Zhang, Xinying ^{[1
]}

机构：

[1] Henan Normal Univ, Henan Key Lab Environm Control, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Sch Environm, Xinxiang 453007, Henan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 34期

基金：

中国国家自然科学基金;

关键词：

12H-Benzo[b]xanthen-12-ones; Naphtha[2,3-b]furans; One-pot synthesis; XANTHONES; DERIVATIVES; THIOXANTHONES; HETEROCYCLES; DISCOVERY; ACRIDONES; ARYNES; TWIGS; ACID;

D O I：

10.1016/j.tetlet.2014.07.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot synthesis of 12H-benzo[b]xanthen-12-ones via an oxidant initiated and base promoted tandem reaction of 2-(4-(2-haloaryl)-4-hydroxybut-1-ynyl)benzaldehydes has been developed. By using similar strategy, a one-pot synthesis of naphtha[2,3-b]furans from the cascade reaction of 2-(4-hydroxy-but-1-ynyl)benzaldehydes with 2-bromoacetonitrile or alpha-bromocarbonyl compounds has also been achieved. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4747 / 4752

页数：6

共 31 条

[1] An efficient copper-catalytic system for performing intramolecular O-arylation reactions in aqueous media. New synthesis of xanthones [J].

Barbero, Nekane ;

SanMartin, Raul ;

Dominguez, Esther .

GREEN CHEMISTRY, 2009, 11 (06) :830-836

[2]

Cordell G. A., 1995, J NAT PRODUCTS, V58, P1024

[3] CONVENIENT SYNTHESES OF THE NATURALLY-OCCURRING BENZO[B]XANTHEN-12-ONE BIKAVERIN - X-RAY CRYSTALLOGRAPHIC CONFIRMATION OF THE PRODUCT REGIOCHEMISTRY [J].

DEKONING, CB ;

GILES, RGF ;

ENGELHARDT, LM ;

WHITE, AH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3209-3216

[4] Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-(ω-N,N-diethylaminoamyloxy)-4,5-difluoroxanthone [J].

Dodean, Rozalia A. ;

Kelly, Jane X. ;

Peyton, David ;

Gard, Gary L. ;

Riscoe, Michael K. ;

Winter, Rolf W. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (03) :1174-1183

[5] Furanonaphthoquinones, atraric acid and a benzofuran from the stem barks of Newbouldia laevis [J].

Gormann, R ;

Kaloga, M ;

Li, XC ;

Ferreira, D ;

Bergenthal, D ;

Kolodziej, H .

PHYTOCHEMISTRY, 2003, 64 (02) :583-587

[6] HETEROCYCLIC ORTHO-QUINODIMETHANES IN SYNTHESIS - A DIELS-ALDER APPROACH TO XANTHENE-DERIVED HETEROCYCLES [J].

GRECO, MN ;

RASMUSSEN, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5532-5535

[7]

Halina K., 2012, CURR ORG SYNTH, V9, P529

[8] Cytotoxic Xanthone Constituents of the Stem Bark of Garcinia mangostana (Mangosteen) [J].

Han, Ah-Reum ;

Kim, Jeong-Ah ;

Lantvit, Daniel D. ;

Leonardus, B. S. Kardono ;

Riswan, Soedarsono ;

Chai, Heebyung ;

de Blanco, Esperanza J. Carcache ;

Farnsworth, Norman R. ;

Swanson, Steven M. ;

Kinghorn, A. Douglas .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (11) :2028-2031

[9] Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl)benzaldehydes [J].

He, Yan ;

Zhang, Xinying ;

Shen, Nana ;

Fan, Xuesen .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10178-10191

[10] DESIGN, SYNTHESIS, AND PHARMACOLOGICAL EVALUATION OF POTENT XANTHONE DICARBOXYLIC-ACID LEUKOTRIENE-B4 RECEPTOR ANTAGONISTS [J].

JACKSON, WT ;

BOYD, RJ ;

FROELICH, LL ;

GAPINSKI, DM ;

MALLETT, BE ;

SAWYER, JS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (12) :1726-1734

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