Chemistry of sulfonylmethyl isocyanides. 45. A direct synthesis of 2-(trimethylstannyl)pyrroles from Michael acceptors and stannylated tosylmethyl isocyanide

被引：43

作者：

Dijkstra, HP ^{[1
]}

ten Have, R ^{[1
]}

van Leusen, AM ^{[1
]}

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 16期

关键词：

D O I：

10.1021/jo972216y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.

引用

页码：5332 / 5338

页数：7

共 29 条

[11] STUDIES ON THE SYNTHESIS OF THE ANTITUMOR AGENT CC-1065 - SYNTHESIS OF THE UNPROTECTED CYCLOPROPAPYRROLOINDOLE A PORTION USING THE 3,3'-BIPYRROLE STRATEGY [J].

MAGNUS, P ;

GALLAGHER, T ;

SCHULTZ, J ;

OR, YS ;

ANANTHANARAYAN, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2706-2711

[12] PREPARATION AND LITHIATION OF N-(N,N-DIMETHYLAMINO)PYRROLE - A USEFUL REAGENT FOR THE PREPARATION OF 2-ACYLPYRROLES [J].

MARTINEZ, GR ;

GRIECO, PA ;

SRINIVASAN, CV .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18) :3760-3761

[13] An unexpected trimethylstannylpyrrole from a stannylated derivative of tosylmethyl isocyanide (TosMIC) and chalcone [J].

Meetsma, A ;

Dijkstra, HP ;

tenHave, R ;

vanLeusen, AM .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 (pt 11) :2747-2750

[14] CHEMISTRY OF SULFONYLMETHYL ISOCYANIDES .30. A NEW SYNTHESIS OF INDOLES BY ELECTROCYCLIC RING-CLOSURE OF DIALKENYLPYRROLES - SYNTHESIS OF ALKENYLPYRROLES FROM 1-TOSYLALKENYL ISOCYANIDES AND MICHAEL ACCEPTORS [J].

MOSKAL, J ;

VANLEUSEN, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4131-4139

[15]

POSSEL O, 1977, HETEROCYCLES, V7, P77

[16] THERMOLYTIC REMOVAL OF TERT-BUTYLOXYCARBONYL (BOC) PROTECTING GROUP ON INDOLES AND PYRROLES [J].

RAWAL, VH ;

CAVA, MP .

TETRAHEDRON LETTERS, 1985, 26 (50) :6141-6142

[17] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].

STILLE, JK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523

[18] A novel synthesis of 3-nitroindoles via electrocyclization of 2,3-(dialk-1-enyl)4-nitropyrroles [J].

ten Have, R ;

van Leusen, AM .

TETRAHEDRON, 1998, 54 (09) :1913-1920

[19]

tenHave R, 1996, SYNTHESIS-STUTTGART, P871

[20] THE PRINCIPAL ELECTRONIC ABSORPTION BANDS OF THE VINYLOGOUS SERIES DERIVED FROM BENZYLALDEHYDE AND BENZOPHENONE [J].

THOMAS, JF ;

BRANCH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (19) :4793-4802

← 1 2 3 →