Traceless solid-phase synthesis of 5-benzoylbenzimidazoles

2001 ◽  
Vol 79 (11) ◽  
pp. 1556-1561 ◽  
Author(s):  
Kyung Joo Lee ◽  
Kim D Janda
Keyword(s):  
Nitro Group ◽  
Functional Group ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Oxidative Cyclization ◽  
One Pot ◽  
Phase Synthesis ◽  
Benzyl Cyanide ◽  
Polymer Supported

A traceless linker strategy for the solid-supported synthesis of 5-benzoylbenzimidazoles has been developed. A benzyl cyanide functional group was linked to 2% divinylbenzene cross-linked polystyrene through a dimethylsilyl linker. Coupling with 5-chloro-2-nitroaniline followed by oxidative decyanation gave benzophenone 11 as a key intermediate in an efficient one-pot reaction procedure. After reduction of the nitro group and oxidative cyclization with a variety of aldehydes in the presence of DDQ, a series of polymer-supported benzimidazoles was produced. Final traceless cleavage of the arylsilane linker with TBAF provided a small library of 5-benzoylbenzimidazoles.Key words: solid-support, traceless linker, arylsilane, 5-benzoylbenzimidazole.

Facile one-step solid-phase synthesis of multitopic organic–DNA hybrids via “click” chemistry

2014 ◽  
Vol 5 (3) ◽  
pp. 1091-1096 ◽  
Author(s):  
Ryan V. Thaner ◽  
Ibrahim Eryazici ◽  
Omar K. Farha ◽  
Chad A. Mirkin ◽  
SonBinh T. Nguyen
Keyword(s):  
Click Chemistry ◽  
Small Molecule ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
One Pot ◽  
Phase Synthesis ◽  
One Step

Small molecule–DNA hybrids can be synthesized in a one-pot fashion and in good yields by coupling multiazide cores to alkyne-modified DNAs on a solid support using click chemistry.

A facile one-pot solid-phase synthesis of oxazolidin-2-ones using polymer-supported 2-hydroxyalkyl selenide reagent

2007 ◽  
Vol 2007 (2) ◽  
pp. 74-75 ◽  
Author(s):  
Qiao-Sheng Hu ◽  
Shou-Ri Sheng ◽  
Shu-Ying Lin ◽  
Mei-Hong Wei ◽  
Qin Xin ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
One Pot ◽  
Phase Synthesis ◽  
Polymer Supported

Solid-phase synthesis of (Z)-allyl iodides from 3-acetoxy-2-methylene-alkanoates with recyclable polymer-supported selenium bromide

2007 ◽  
Vol 18 (4) ◽  
pp. 377-379 ◽  
Author(s):  
Shou Ri Sheng ◽  
Ming Gang Hu ◽  
Qin Xin ◽  
Xiao Ling Liu ◽  
Xian Huang
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Polymer Supported

One pot solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)-ones on Rinkamide-resin

Tetrahedron ◽  
2005 ◽  
Vol 61 (1) ◽  
pp. 205-211 ◽  
Author(s):  
Michael Sax ◽  
Stefanie Berning ◽  
Bernhard Wünsch
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
One Pot ◽  
Phase Synthesis

scholarly journals The Breaking Beads Approach for Photocleavage from Solid Support

2020 ◽  
Author(s):  
yasmeen bakhatan ◽  
Israel Alshanski ◽  
Dana Grunhaus ◽  
Mattan Hurevich
Keyword(s):  
Continuous Flow ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
High Energy ◽  
Solid Support ◽  
Phase Synthesis ◽  
Polystyrene Beads ◽  
Magnetic Stirring ◽  
Photolabile Linkers

Photocleavage from polystyrene beads is a pivotal reaction for solid phase synthesis that relies on photolabile linkers. The photocleavage, usually performed by batch irradiation, suffers from incomplete and slow cleavage. To overcome these issues, continuous flow and high-energy lamps are frequently used, but these setups are hazardous, technically challenging, and expensive. We developed a photocleavage approach that relies on a benchtop LED lamp and magnetic stirring. In this approach, we crush the beads instead of keeping their integrity to increase the yield of photocleavage. This approach proved very efficient for photocleavage of protected oligosaccharides.

A New Linker for Solid-Phase Synthesis of Oligonucleotides with Terminal Phosphate Group

2008 ◽  
Vol 73 (1) ◽  
pp. 32-43 ◽  
Author(s):  
Ondřej Pačes ◽  
Zdeněk Točík ◽  
Ivan Rosenberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Phosphate Group ◽  
Phase Synthesis ◽  
Terminal Phosphate Group

Synthesis of a novel cyanoethyl-type linker suitable for the solid-phase synthesis of oligodeoxynucleotides possessing terminal 3'-phosphate group is described. Since the linker is a 2-substituted 2-cyanoethanol, the release of the synthesized oligonucleotide from the solid support is accomplished by β-elimination in the ammonia deprotection step.

Efficient One-Pot Formation of Amides from Benzyl Carbamates: Application to Solid-Phase Synthesis

Tetrahedron ◽  
2000 ◽  
Vol 56 (45) ◽  
pp. 8867-8875 ◽  
Author(s):  
Wen-Ren Li ◽  
Ying-Chih Yo ◽  
Yu-Sheng Lin
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
One Pot ◽  
Phase Synthesis

Polymer supported calixarene derivative useful for solid-phase synthesis application

2010 ◽  
Vol 51 (47) ◽  
pp. 6139-6142 ◽  
Author(s):  
Giuseppe Granata ◽  
Grazia M.L. Consoli ◽  
Sebastiano Sciuto ◽  
Corrada Geraci
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Calixarene Derivative ◽  
Polymer Supported
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