Nickel-catalyzed highly regio- and stereoselective cyclization of oxanorbornenes with alkyl propiolates: A novel method for the synthesis of benzocoumarin derivatives

被引：0

作者：

Rayabarapu, DK ^{[1
]}

Sambaiah, T ^{[1
]}

Cheng, CH ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2001年 / 40卷 / 07期

关键词：

alkenes; coumarins; cyclization; nickel;

D O I：

10.1002/1521-3773(20010401)40:7<1286::AID-ANIE1286>3.0.CO;2-I

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

7-Oxabenzonorbornadienes bearing various substituents react with propiolates in the presence of [NiBr2(dppe)] (dppe = bis(diphenylphosphanyl)ethane) as a catalyst precursor and zinc powder to give benzocoumarin derivatives [Eq. (1)]. The one-pot reactions proceed at 80°C in acetonitrile, and the products are obtained in good yields with high regio- and stereoselectivity.

引用

收藏

页码：1286 / +

页数：4

相关论文

共 37 条

[1] SYNTHETIC STUDIES ON WORTMANNIN AND 11-DESACETOXYWORTMANNIN [J].

BROKA, CA ;

RUHLAND, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4888-4894

[2] SYNTHESIS VIA PUMMERER INTERMEDIATES .4. SYNTHESIS OF 1-(4-HYDROXY-2-OXO-2H-1-BENZOPYRAN-3-YL)PYRIDINIUM HYDROXIDE INNER SALT DERIVATIVES AND 3-(2H)BENZOFURANONES BY THE ACTION OF PHOSGENE IN PYRIDINE ON 2-HYDROXY-1-[(METHYLSULFINYL)ACETYL]BENZENE DERIVATIVES [J].

CONNOR, DT ;

SORENSON, RJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :587-590

[3] Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides [J].

Feng, CC ;

Nandi, M ;

Sambaiah, T ;

Cheng, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3538-3543

[4] Metal-assisted cycloaddition reactions in organotransition metal chemistry [J].

Fruhauf, HW .

CHEMICAL REVIEWS, 1997, 97 (03) :523-596

[5]

GORELIK E, 1987, CANCER RES, V47, P809

[6]

GROTJAHN DB, 1995, COMPREHENSIVE ORGA 2, V12, P703

[7] A concise synthesis of arnottin I via internal biaryl coupling reaction using palladium reagent [J].

Harayama, T ;

Yasuda, H .

HETEROCYCLES, 1997, 46 :61-64

[8] Nickel-promoted first ene-diyne cycloaddition reaction on C60:: Synthesis and photochemistry of the fullerene derivatives [J].

Hsiao, TY ;

Santhosh, KC ;

Liou, KF ;

Cheng, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12232-12236

[9] Nickel-catalyzed cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes: reaction with multiple synthetic applications [J].

Huang, DJ ;

Sambaiah, T ;

Cheng, CH .

NEW JOURNAL OF CHEMISTRY, 1998, 22 (11) :1147-1149

[10]

Huang DJ, 2000, CHEM-EUR J, V6, P3706, DOI 10.1002/1521-3765(20001016)6:20<3706::AID-CHEM3706>3.0.CO

← 1 2 3 4 →