Automated flow-through synthesis of heterocyclic thioethers

被引：26

作者：

Jönsson, D ^{[1
]}

Warrington, BH ^{[1
]}

Ladlow, M ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, GlaxoSmithKline Cambridge Technol Ctr, Cambridge CB2 1EW, England

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2004年 / 6卷 / 04期

关键词：

D O I：

10.1021/cc0499486

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The fully automated, sequential flow-through synthesis of a 44-member array of thioethers 10{1-4, 1-11} employing a resin "capture and release" reactor column is described. The array incorporates four different heterocyclic scaffolds, and the synthesis was performed using a custom-built robotic synthesizer that is able to (i) load and regenerate the reactor column and (ii) array each product into a single vial using UV threshold detection. All the compounds were obtained in high yield (>75%) and excellent purity (>95%) without the need for further purification.

引用

页码：584 / 595

页数：12

共 51 条

[1] A convenient 'catch and release' synthesis of fused 2-alkylthio-pyrimidinones mediated by polymer-bound BEMP [J].

Adams, GL ;

Graybill, TL ;

Sanchez, RM ;

Magaard, VW ;

Burton, G ;

Rivero, RA .

TETRAHEDRON LETTERS, 2003, 44 (27) :5041-5045

[2] Convenient preparation and use of a new analytical construct for the analysis and development of solid-phase chemistries [J].

Andrews, SP ;

Ladlow, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5525-5533

[3] Polymer-supported reagents for multi-step organic synthesis: Application to the synthesis of sildenafil [J].

Baxendale, IR ;

Ley, SV .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) :1983-1986

[4] A concise synthesis of carpanone using solid-supported reagents and scavengers [J].

Baxendale, IR ;

Lee, AL ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16) :1850-1857

[5] Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents [J].

Baxendale, IR ;

Ley, SV ;

Nessi, M ;

Piutti, C .

TETRAHEDRON, 2002, 58 (32) :6285-6304

[6] Synthesis of an array of potential matrix metalloproteinase inhibitors using a sequence of polymer-supported reagents [J].

Caldarelli, M ;

Habermann, J ;

Ley, SV .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) :2049-2052

[7]

DORWALD FZ, 2000, ORGANIC SYNTHESIS SO

[8]

Drewry DH, 1999, MED RES REV, V19, P97, DOI 10.1002/(SICI)1098-1128(199903)19:2<97::AID-MED2>3.0.CO

[9]

2-Y

[10]

Flynn DL, 2002, CURR OPIN DRUG DI DE, V5, P580

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