Synthesis of new aryl substituted furan-2(5H)-ones using the Suzuki-Miyaura reaction

被引：12

作者：

Zhang, Ruonan ^{[1
]}

Iskander, George ^{[1
]}

da Silva, Paulo ^{[1
]}

Chan, Daniel ^{[1
]}

Vignevich, Valentina ^{[1
]}

Vi Nguyen ^{[1
]}

Bhadbhade, Mohan M. ^{[1
]}

Black, David StC ^{[1
]}

Kumar, Naresh ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Analyt Ctr, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON | 2011年 / 67卷 / 16期

基金：

澳大利亚研究理事会;

关键词：

Furanone; Suzuki-Miyaura; Fimbrolide; Antibacterial; CROSS-COUPLING REACTIONS; RESISTANCE; BACTERIA; FURANONES; ACCESS; SIGNAL;

D O I：

10.1016/j.tet.2011.02.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel 5-arylidenefuran-2(5H)-ones and 5-arylidene-4-arylfuran-2(5H)-ones were synthesized via the Suzuki Miyaura reactions of fimbrolide derivatives 5-(bromomethylene)furan-2(5H)-one and 4-bromo-5-(bromomethylene)furan-2(5H)-one, respectively. A regioselective Suzuki Miyaura reaction on 4-bromo-5-(bromomethylene)furan-2(5H)-one allowed the synthesis of unsymmetrically substituted 5-arylidene-4-arylfuran-2(5H)-ones. The crystal structure of the intermediate 5-arylidene-4-bromofuran-2 (5H)-one revealed interesting Br center dot center dot center dot O halogen bonding. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3010 / 3016

页数：7

共 25 条

[1] Resistance to antibiotics: Are we in the post-antibiotic era? [J].

Alanis, AJ .

ARCHIVES OF MEDICAL RESEARCH, 2005, 36 (06) :697-705

[2] Halogen bonds in biological molecules [J].

Auffinger, P ;

Hays, FA ;

Westhof, E ;

Ho, PS .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (48) :16789-16794

[3] Facile access to 4-aryl-2(5H)-furanones by Suzuki cross coupling:: Efficient synthesis of rubrolides C and E [J].

Boukouvalas, J ;

Lachance, N ;

Ouellet, M ;

Trudeau, M .

TETRAHEDRON LETTERS, 1998, 39 (42) :7665-7668

[4]

de Nys R, 2006, MAR MOL BIOTECHNOL, V42, P55

[5] QUORUM SENSING IN BACTERIA - THE LUXR-LUXI FAMILY OF CELL DENSITY-RESPONSIVE TRANSCRIPTIONAL REGULATORS [J].

FUQUA, WC ;

WINANS, SC ;

GREENBERG, EP .

JOURNAL OF BACTERIOLOGY, 1994, 176 (02) :269-275

[6] Eukaryotic interference with homoserine lactone-mediated prokaryotic signaling [J].

Givskov, M ;

DeNys, R ;

Manefield, M ;

Gram, L ;

Maximilien, R ;

Eberl, L ;

Molin, S ;

Steinberg, PD ;

Kjelleberg, S .

JOURNAL OF BACTERIOLOGY, 1996, 178 (22) :6618-6622

[7] Attenuation of Pseudomonas aeruginosa virulence by quorum sensing inhibitors [J].

Hentzer, M ;

Wu, H ;

Andersen, JB ;

Riedel, K ;

Rasmussen, TB ;

Bagge, N ;

Kumar, N ;

Schembri, MA ;

Song, ZJ ;

Kristoffersen, P ;

Manefield, M ;

Costerton, JW ;

Molin, S ;

Eberl, L ;

Steinberg, P ;

Kjelleberg, S ;

Hoiby, N ;

Givskov, M .

EMBO JOURNAL, 2003, 22 (15) :3803-3815

[8] Inhibition of quorum sensing in Pseudomonas aeruginosa biofilm bacteria by a halogenated furanone compound [J].

Hentzer, M ;

Riedel, K ;

Rasmussen, TB ;

Heydorn, A ;

Andersen, JB ;

Parsek, MR ;

Rice, SA ;

Eberl, L ;

Molin, S ;

Hoiby, N ;

Kjelleberg, S ;

Givskov, M .

MICROBIOLOGY-SGM, 2002, 148 :87-102

[9]

KUMAR N, 2008, Patent No. 2008040097

[10] Fimbrolide disulfanes: synthesis and crystal interactions [J].

Kutty, Samuel K. ;

Bhadbhade, Mohan M. ;

Iskander, George ;

Bishop, Roger ;

Griffith, Renate ;

Black, David StC. ;

Kumar, Naresh .

TETRAHEDRON LETTERS, 2010, 51 (37) :4856-4858

← 1 2 3 →