Transition-Metal-Free Approach to Polysubstituted Furans

被引：25

作者：

You, Changming ^{[1
]}

Zhang, Zhenming ^{[1
]}

Tu, Yongliang ^{[1
]}

Tang, Hong ^{[1
]}

Wang, Yuanfeng ^{[1
]}

Long, Da ^{[1
]}

Zhao, Junfeng ^{[1
,2
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

[2] Guangzhou Med Univ, Sch Pharmaceut Sci, Guangzhou 511436, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期

基金：

中国国家自然科学基金;

关键词：

HIGHLY FUNCTIONALIZED BENZOFURANS; REGIOSELECTIVE SYNTHESIS; H FUNCTIONALIZATION; EFFICIENT; STRATEGY; TANDEM; HYDROXYPHENONES; CONSTRUCTION; CYCLIZATION;

D O I：

10.1021/acs.joc.9b03006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of beta-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance.

引用

页码：3902 / 3910

页数：9

共 46 条

[1] An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes [J].

Albrecht, Lukasz ;

Ransborg, Lars Krogager ;

Gschwend, Bjorn ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) :17886-17893

[2] One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents 'Na2CO3/Al2O3-PPA/SiO2' [J].

Aoyama, Tadashi ;

Nagaoka, Takashi ;

Takido, Toshio ;

Kodomari, Mitsuo .

SYNTHESIS-STUTTGART, 2011, (04) :619-625

[3] TRANSITION-METAL DIHALOCARBENE COMPLEXES [J].

BROTHERS, PJ ;

ROPER, WR .

CHEMICAL REVIEWS, 1988, 88 (07) :1293-1326

[4] NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES [J].

CARINI, DJ ;

DUNCIA, JV ;

ALDRICH, PE ;

CHIU, AT ;

JOHNSON, AL ;

PIERCE, ME ;

PRICE, WA ;

SANTELLA, JB ;

WELLS, GJ ;

WEXLER, RR ;

WONG, PC ;

YOO, SE ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2525-2547

[5] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems [J].

Chelucci, Giorgio .

CHEMICAL REVIEWS, 2012, 112 (03) :1344-1462

[6] A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions [J].

Chen, Ko-Wei ;

Syu, Siang-en ;

Jang, Yeong-Jiunn ;

Lin, Wenwei .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2098-2106

[7] Organocatalytic Synthesis of Highly Substituted Furfuryl Alcohols and Amines [J].

Clark, J. Stephen ;

Boyer, Alistair ;

Aimon, Anthony ;

Garcia, Paloma Engel ;

Lindsay, David M. ;

Symington, Andrew D. F. ;

Danoy, Yves .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12128-12131

[8] Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate [J].

Coutant, Eloi P. ;

Hervin, Vincent ;

Gagnot, Glwadys ;

Ford, Candice ;

Baatallah, Racha ;

Janin, Yves L. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :2853-2860

[9] Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles [J].

Dudnik, Alexander S. ;

Sromek, Anna W. ;

Rubina, Marina ;

Kim, Joseph T. ;

Kel'in, Alexander V. ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1440-1452

[10]

FREY H, 1993, SYNLETT, P905

← 1 2 3 4 5 →