Copper(I) Iodide Mediated Iodocyclization of Cyclopropylideneallenyl Ketones: Facile and Effective Synthesis of Highly Substituted Furan Derivatives

被引：18

作者：

Miao, Maozhong ^{[1
]}

Xu, Xin ^{[1
]}

Xu, Lijun ^{[1
]}

Ren, Hongjun ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 27期

基金：

中国国家自然科学基金;

关键词：

Synthetic methods; Copper; Cross-coupling; Cyclization; Oxygen heterocycles; Small ring systems; EFFICIENT SYNTHESIS; ALLENYL KETONES; CYCLIZATION; ACIDS; CYCLOISOMERIZATION; TRANSFORMATION; 1,2-MIGRATION; REARRANGEMENT; CONSTRUCTION; GENERATION;

D O I：

10.1002/ejoc.201402823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic cyclization of cyclopropylideneallenyl ketones in the presence of I2/CuI offers an efficient and straightforward route to highly substituted furans under mild reaction conditions. Further transformation of the resulting iodofurans provides structurally more advanced furan derivatives.

引用

页码：5896 / 5900

页数：5

共 67 条

[1]

[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.200390001

[2]

[Anonymous], 2008, Comprehensive Heterocyclic Chemistry III

[3] Synthesis of methylene- and alkylidenecyclopropane derivatives [J].

Brandi, A ;

Goti, A .

CHEMICAL REVIEWS, 1998, 98 (02) :589-635

[4] Heterocycles from alkylidenecyclopropanes [J].

Brandi, A ;

Cicchi, S ;

Cordero, FM ;

Goti, A .

CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269

[5] A synthesis strategy yielding skeletally diverse small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :14095-14104

[6]

Butin A. V., 2011, SYNTHESIS-STUTTGART, V16, P2629

[7] Furan ring opening-pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines [J].

Butin, Alexander V. ;

Nevolina, Tatyana A. ;

Shcherbinin, Vitaly A. ;

Trushkov, Igor V. ;

Cheshkov, Dmitry A. ;

Krapivin, Gennady D. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (14) :3316-3327

[8] Furan Ring-Opening/Indole Ring-Closure: Pictet-Spengler-Like Reaction of 2-(o-Aminophenyl)furans with Aldehydes [J].

Butin, Alexander V. ;

Uchuskin, Maxim G. ;

Pilipenko, Arkady S. ;

Tsiunchik, Fatima A. ;

Cheshkov, Dmitry A. ;

Trushkov, Igor V. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (05) :920-926

[9] Heterocycles from cyclopropanes: applications in natural product synthesis [J].

Carson, Cheryl A. ;

Kerr, Michael A. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060

[10] Palladium-Catalyzed Highly Regioselective [3+2] Cycloaddition Reactions of Alkylidenecyclopropa[b]naphthalenes with Alkenes or Alkynes: An Efficient Synthesis of 1(3)-Alkylidene-2,3-dihydro-1H-benzo[f]indenes and 1-Alkylidene-1H-benzo[f]indenes [J].

Chen, Wanli ;

Cao, Jian ;

Huang, Xian .

ORGANIC LETTERS, 2008, 10 (24) :5537-5540

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