Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement

被引：30

作者：

Gopi, Elumalai ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 03期

关键词：

ELECTROPHILIC CYCLIZATION; GEM-DIHALOCYCLOPROPANES; CYCLOPROPANATION; HETEROCYCLES; DERIVATIVES; FURANS;

D O I：

10.1021/jo3022988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.

引用

页码：910 / 919

页数：10

共 72 条

[1] ALUMINUM-OXIDE ASSISTED STEREOSELECTIVE REARRANGEMENT OF A CYCLOPROPYL KETONE TO 4,5-DIHYDROFURAN [J].

ALONSO, ME ;

MORALES, A .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) :4530-4532

[2] Thermal rearrangements of vinylcyclopropanes to cyclopentenes [J].

Baldwin, JE .

CHEMICAL REVIEWS, 2003, 103 (04) :1197-1212

[3]

Banwell M.G., 1991, ADV STRAIN ORGANIC C, V1, P19

[4] New processes for the synthesis of biologically relevant heterocycles [J].

Banwell, Martin G. .

PURE AND APPLIED CHEMISTRY, 2008, 80 (04) :669-679

[5] New methods for the synthesis of certain alkaloids and terpenoids [J].

Banwell, Martin G. ;

Lehmann, Anna L. ;

Menon, Rajeev S. ;

Willis, Anthony C. .

PURE AND APPLIED CHEMISTRY, 2011, 83 (03) :411-423

[6] Pyrroles and gem-dihalocyclopropanes as building blocks for alkaloid synthesis [J].

Banwell, MG ;

Beck, DAS ;

Stanislawski, PC ;

Sydnes, MO ;

Taylor, RM .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1589-1600

[7] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi [J].

Banwell, MG ;

Edwards, AJ ;

Jolliffe, KA ;

Smith, JA ;

Hamel, E ;

Verdier-Pinard, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :296-305

[8]

BARLET R, 1969, B SOC CHIM FR, P3729

[9] Mechanochemically triggered bond formation in solid-state polymers [J].

Black, Ashley L. ;

Orlicki, Joshua A. ;

Craig, Stephen L. .

JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (23) :8460-8465

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

Carson, Cheryl A. ;

Kerr, Michael A. .

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

← 1 2 3 4 5 6 7 8 →