Regioselective Synthesis of 2-(Aryloxythio)benzoates by the First [3+3] Cyclizations of 3-Aryloxythio-1-silyloxybuta-1,3-dienes with 3-Alkoxy-2-en-1-ones

被引：9

作者：

Iqbal, Inam ^{[1
]}

Imran, Muhammad ^{[1
]}

Villinger, Alexander ^{[1
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 02期

关键词：

cyclizations; diaryl sulfides; regioselectivity; pyridines; silyl enol ethers; ENOL SILYL ETHERS; DIARYL SULFIDES; CYCLOAROMATIZATION REACTION; ARYL HALIDES; SULFUR; CHEMISTRY; THIOLS; BENZOPENTATHIEPIN; ALKALOIDS; CATALYST;

D O I：

10.1055/s-0028-1083287

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized 2-(aryloxythio)benzoates were regioselectively prepared by the first [3+3] cyclizations of 3-aryloxythiol-trimethylsilyloxybuta-1,3-dienes with 3-alkoxy-2-en-1-ones.

引用

页码：297 / 305

页数：9

共 32 条

[1] PALLADIUM-CATALYZED AROYLATION OF ALKYL VINYL ETHERS - AN ENTRY TO MONOPROTECTED 1-ARYL-1,3-DICARBONYL EQUIVALENTS [J].

ANDERSSON, CM ;

HALLBERG, A .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4257-4263

[2] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[3]

Baxter I, 2000, CHEM-EUR J, V6, P4285, DOI 10.1002/1521-3765(20001201)6:23<4285::AID-CHEM4285>3.3.CO

[4]

2-4

[5] TOTAL SYNTHESIS OF THE NOVEL BENZOPENTATHIEPIN VARACINIUM TRIFLUOROACETATE - THE VIABILITY OF VARACIN FREE-BASE [J].

BEHAR, V ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7017-7018

[6] CHEMISTRY OF ENOL SILYL ETHERS - A GENERAL-SYNTHESIS OF 3-HYDROXYHOMOPHTHALATES AND A BIOMIMETIC SYNTHESIS OF SCLERIN .12. [J].

BROWNBRIDGE, P ;

CHAN, TH ;

BROOK, MA ;

KANG, GJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (04) :688-693

[7]

*CCDC, 700707 CCDC

[8] CHEMISTRY OF 1-(TRIMETHYLSILOXY)-1-METHOXY-3-[ALKYL(ARYL)THIO]-1,3-BUTADIENES AND THE SYNTHESIS OF ARYL SULFIDES VIA A CYCLOAROMATIZATION REACTION [J].

CHAN, TH ;

PRASAD, CVC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3012-3016

[9] A NEW 4C+2C ANNELATION REACTION BASED ON TANDEM MICHAEL-CLAISEN CONDENSATION .1. GENERAL SCOPE [J].

CHAN, TH ;

PRASAD, CVC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :110-119

[10] CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].

CHAN, TH ;

BROWNBRIDGE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538

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