A new method for the synthesis of plurisubstituted pyrroles

被引：40

作者：

Bashiardes, G ^{[1
]}

Safir, I ^{[1
]}

Barbot, F ^{[1
]}

Laduranty, J ^{[1
]}

机构：

[1] Univ Poitiers, Dept Chem, SFA, UMR 6514, F-86022 Poitiers, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 46期

关键词：

D O I：

10.1016/j.tetlet.2003.09.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile method for the synthesis of pyrroles is described using an intramolecular [3+2] cycloaddition reaction. This method allows the expedient preparation of 'plurisubstituted' compounds in which functionality is incorporated by choice, using appropriate readily available starting materials. Polycyclic pyrrole derivatives as well as 2-aryl monocyclic analogues are described. Several families of compounds are synthesized by sequential transformations. The method is designed to allow the creation of libraries with increased diversity of functionality by combinatorial or parallel synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8417 / 8420

页数：4

共 11 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .19. INTRAMOLECULAR CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE YLIDES GENERATED VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS
ARDILL, H
GRIGG, R
SRIDHARAN, V
SURENDRAKUMAR, S
[J]. TETRAHEDRON, 1988, 44 (15) : 4953 - 4966
[2] EIDEN F, 1983, LIEBIGS ANN CHEM, P165
[3] Synthesis of 2,3,5-substituted pyrrole derivatives
Ferreira, PMT
Maia, HLS
Monteiro, LS
[J]. TETRAHEDRON LETTERS, 2002, 43 (25) : 4491 - 4493
[4] Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core
Fürstner, A
Krause, H
Thiel, OR
[J]. TETRAHEDRON, 2002, 58 (32) : 6373 - 6380
[5] TANDEM GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDES WITH ALKYNE DIPOLAROPHILES
HARWOOD, LM
KITCHEN, LC
[J]. TETRAHEDRON LETTERS, 1993, 34 (41) : 6603 - 6606
[6] Short and flexible route to 3,4-diarylpyrrole marine alkaloids: syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether
Iwao, M
Takeuchi, T
Fujikawa, N
Fukuda, T
Ishibashi, F
[J]. TETRAHEDRON LETTERS, 2003, 44 (24) : 4443 - 4446
[7] Efficient one-pot synthesis of polysubstituted pyrroles
Katritzky, AR
Huang, TB
Voronkov, MV
Wang, MY
Kolb, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8819 - 8821
[8] Total syntheses of the marine pyrrole alkaloids polycitone A and B
Kreipl, AT
Reid, C
Steglich, W
[J]. ORGANIC LETTERS, 2002, 4 (19) : 3287 - 3288
[9] Ogawa H, 1996, HETEROCYCLES, V42, P75
[10] PATEL AV, 1997, RODDS CHEM CARBON CO, V4, pCH4

← 1 2 →