Synthesis of Coumestan Derivatives via FeCl3-Mediated Oxidative Ring Closure of 4-Hydroxy Coumarins

被引：69

作者：

Tang, Lina ^{[1
]}

Pang, Yongle ^{[1
]}

Yan, Qiao ^{[1
]}

Shi, Liuqing ^{[1
]}

Huang, Jianhui ^{[1
]}

Du, Yunfei ^{[1
]}

Zhao, Kang ^{[1
]}

机构：

[1] Tianjin Univ, Tianjin Key Lab Modern Drug Delivery & High Effic, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期

基金：

中国国家自然科学基金;

关键词：

COUPLING REACTIONS; HETEROCYCLIC-COMPOUNDS; EFFICIENT SYNTHESIS; WEDELOLACTONE; CYCLIZATION; BENZOFURAN; CHLORIDE;

D O I：

10.1021/jo2000644

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient approach to the syntheses of coumestan analogues has been developed. The underpinning strategy involves a FeCl3-mediated direct intramolecular oxidative annellation of 4-hydroxy-3-phenyl-2H-chromen-2-one derivatives. Utilizing this synthetic protocol, a variety of coumestan derivatives were conveniently obtained from readily available reagents.

引用

页码：2744 / 2752

页数：9

共 67 条

[1] A new short synthesis of coumestrol and its application for the synthesis of [6,6a,11a-13C3]coumestrol [J].

Al-Maharik, N ;

Botting, NP .

TETRAHEDRON, 2004, 60 (07) :1637-1642

[2]

[Anonymous], 1999, END DISR SCI PERSP

[3] THE CHEMISTRY OF THE INSOLUBLE RED WOODS .4. SOME MIXED BENZOINS [J].

BADCOCK, GG ;

CAVILL, GWK ;

ROBERTSON, A ;

WHALLEY, WB .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV) :2961-2965

[4] Selective cleavage of isopropyl aryl ethers by aluminum trichloride [J].

Banwell, MG ;

Flynn, BL ;

Stewart, SG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9139-9144

[5] APPLICATION OF ARYLLEAD(IV) DERIVATIVES TO THE PREPARATION OF 3-ARYL-4-HYDROXY-1-BENZOPYRAN-2-ONES [J].

BARTON, DHR ;

DONNELLY, DMX ;

FINET, JP ;

GUIRY, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1365-1375

[6] THE CHEMISTRY OF THE INSOLUBLE RED WOODS .2. A NEW SYNTHESIS OF 4-HYDROXYCOUMARINS [J].

BOYD, J ;

ROBERTSON, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (FEB) :174-176

[7] FLAVONOID EPOXIDES .17. STEREOSPECIFIC SYNTHESIS AND ACID-CATALYZED REARRANGEMENT OF AURONE EPOXIDES [J].

BRADY, BA ;

HEALY, MM ;

OSULLIVAN, WI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (06) :1151-1155

[8]

Bushby RJ, 2001, SYNTHESIS-STUTTGART, P763

[9] Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0)-catalysis and oxidative-cyclization [J].

Chang, Chia-Fu ;

Yang, Ling-Yi ;

Chang, Shiao-Wei ;

Fang, Yu-Ting ;

Lee, Yean-Jang .

TETRAHEDRON, 2008, 64 (17) :3661-3666

[10]

Cyril L. H., 2000, TETRAHEDRON, V56, P295

← 1 2 3 4 5 6 7 →