Protection of poorly nucleophilic pyrroles

被引：34

作者：

Handy, ST ^{[1
]}

Sabatini, JJ ^{[1
]}

Zhang, Y ^{[1
]}

Vulfova, I ^{[1
]}

机构：

[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 26期

关键词：

halogenation; pyrrole; protecting groups; carbamate;

D O I：

10.1016/j.tetlet.2004.04.178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the introduction of carbamate protecting groups on the ring nitrogen of electron-deficient pyrroles has been developed using the commercially available chloroformates and stoichiometric tetralbutylammonium iodide. The method is postulated to generate the more reactive iodoformates in situ to facilitate these protection reactions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5057 / 5060

页数：4

相关论文

共 15 条

[1]

[Anonymous], 1984, ANGEW CHEM

[2] OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].

ARTIS, DR ;

CHO, IS ;

JAIMEFIGUEROA, S ;

MUCHOWSKI, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466

[3] Synthesis of the first fluorinated bilirubin [J].

Boiadjiev, SE ;

Lightner, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :399-404

[4] Divergent pathways in the intramolecular reactions between rhodium-stabilized vinylcarbenoids and pyrroles: Construction of fused tropanes and 7-azabicyclo[4.2.0] octadienes [J].

Davies, HML ;

Matasi, JJ ;

Ahmed, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2305-2313

[5] SOME MERCURATION REACTIONS OF SUBSTITUTED PYRROLES [J].

GANSKE, JA ;

PANDEY, RK ;

POSTICH, MJ ;

SNOW, KM ;

SMITH, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4801-4807

[6] Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole [J].

Gilchrist, TL ;

Lemos, A ;

Ottaway, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (20) :3005-3012

[7]

GREENE TW, 1999, PROTECTIVE GROUPS OR, P617

[8] VILSMEIER-HAACK REACTION WITH SUCCINAMIDALS - A CONVENIENT SYNTHESIS OF 5-CHLOROPYRROLE-2-CARBOXALDEHYDES AND 5-CHLOROPYRROLE-2,4-DICARBOXALDEHYDES [J].

GUZMAN, A ;

ROMERO, M ;

MUCHOWSKI, JM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (05) :791-794

[9] An unusual dehalogenation in the Suzuki coupling of 4-bromopyrrole-2-carboxylates [J].

Handy, ST ;

Bregman, H ;

Lewis, J ;

Zhang, XL ;

Zhang, YN .

TETRAHEDRON LETTERS, 2003, 44 (03) :427-430

[10] REACTIVE IODINE COMPOUNDS-8 .7. SYNTHESIS AND CUCN-PROMOTED CYANATION OF IODOFORMIC ESTERS [J].

HOFFMANN, HMR ;

IRANSHAHI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) :1174-1176