MAOS User Group Meeting Presentations
Click on the User Group Meeting location below to jump to the presentation PDF handouts. To download a PDF presentation, click on the specific presentation. Not all presentation are available for download at the author's request.


Boston – May 26, 2005

San Diego – October 11, 2005

Plymouth, PA - October 13, 2005
 

Boston
Multi-Component Synthesis: Metals, Microwaves, and Microchannels
Michael Organ, Ph.D., York University
In light of the diverse reactivity profile exhibited by Pd, it can be used manipulate substrates possessing multiple functional groups into products via a sequence of queued catalytic reactions. The development of this methodology will be illustrated along with its application to the synthesis of natural products and molecular libraries. Metal complexes of Pd can be irradiated in a microwave reactor to greatly enhance the rate of such chemical transformations. This chemistry will be discussed in addition to the application of irradiation-assisted, metal-catalyzed reactions in microchannel reactors for the preparation of molecular libraries using flow techniques.

The Integration and Application of Microwave Technology into the ArQule AMAP™ Chemistry Platform
Ted Manley, ArQule
An increasing number of publications regarding microwave technology have shown that there are many potential advantages to microwave assisted organic synthesis. Using this technology in conjunction with established high throughput synthesis techniques, chemists have the ability to reduce reaction times, improve yields, and access chemical transformations previously unavailable with traditional, thermal heating methods. To take full advantage of this enabling technology at ArQule, it was necessary to integrate commercially available microwave systems with our existing Automated Molecular Assembly Plant (AMAP™) platform, requiring significant software and hardware modifications to both. This presentation will discuss the challenges with the integration process and the successful application of the technology for high throughput medicinal chemistry.

Microwave Assisted Organic Synthesis and Automated Flash Chromatography as Enabling Tools in Drug Discovery
Shahnaz Ghassemi, Ph.D., Biotage Discovery Chemistry Group
Combining productivity enhancing tools such as microwave synthesis and high-performance flash chromatography significantly speeds up the drug development process. This talk will address the recent advances in combining the MAOS with flash purification for rapid production of organic compound.

Conventional and Microwave Conditions for Lactone Arylation
Scott Malcolm, Ph.D., Fengjiang Wang, Ph.D., Michael Hewitt, Ph.D., and Liming Shao, Ph.D., Sepracor
Various substituted lactones were prepared by arylation under modified Hartwig-Buchwald conditions. In addition, this reaction enjoyed a significant rate acceleration under microwave radiation and some more difficult transformations were accomplished in greater yield. These examples are notable because they were performed without schlenk apparatus, on the benchtop, and on multi-gram scale. 

Microwave Synthesis  in Water
Nicholas Leadbeater, Ph.D., University of Connecticut
The talk will take two parts. The first will be an overview our new work in 2004/5 focused on the development of rapid, easy C-C coupling methodologies using microwave heating. We will focus on new developments in Suzuki and Heck couplings in water showing the versatility of microwave heating. The second will outline our attempts to probe the evidence for and against a non-thermal microwave effect in relation to synthetic organic chemistry by using the method of simultaneous cooling. The effects of microwave heating whilst simultaneously cooling on a range of organic transformations will be discussed. We will also focus on how cooling can be used to prolong the lifetime of organic substrates in Suzuki reactions involving aryl chlorides.

San Diego
Synthesis of New Noscapine Derivatives with Promising Anti-Cancer Activity
Alexander Khvat, Ph.D., Chemical Diversity, Inc.
Noscapine (narcotine) is an opium alkaloid from Papaver somniferum L. Papaveraceae, however narcotic properties of noscapine are totally absent. The unique anticancer properties of noscapine prompt us to begin a systematic study of possible modifications of its structure, in order to obtain new bioactive molecules with remaining stereo¬che¬mi¬stry of noscapine bi-template structures. New approaches to previously unknown derivatives of noscapine have been developed and validated. Several libraries based on new core building blocks (N01-N14) have been design and synthesized. The details of the building blocks and libraries synthesis as well as anti-cancer activity of some derivatives will be discussed.

Microwave Technology: Where Do We Go From Here?
Farah Mavandadi, Ph.D., Biotage AB
Microwave chemistry has now become a well established technique within many discovery chemistry labs. The ability to combine solid-supported reagents and scavengers with microwave technology will offer new opportunities for the organic chemist. This talk will focus on some of those possibilities as these technologies continue to move forward.

Anhydrous Nitronium Triflate Nitration of Heteroaromatic Compounds using Microwave-Assisted Conditions
Scott Shackelford, Ph.D., Air Force Research Laboratory
Anhydrous heteroaromatic nitration with tetramethylammonium nitrate generated nitronium triflate in dichloromethane solvent is a potent, high-yield nitrating method that often affords analytically pure products after a simple aqueous work-up. Applicable to conventional benchtop and accelerated microwave-assisted conditions, past nitration successes will be reviewed and compared. Recent microwave-assisted nitration attempts with 5-membered heterocyclic compounds containing one and two ring heteroatoms will be discussed to assess electrophilic directional effects and relative ring position reactivity.


Plymouth, PA
Microwave Technology: Where Do We Go From Here?
Steve Jordan, Ph.D., Biotage AB
Microwave chemistry has now become a well established technique within many discovery chemistry labs. The ability to combine solid-supported reagents and scavengers with microwave technology will offer new opportunities for the organic chemist. This talk will focus on some of those possibilities as these technologies continue to move forward.

Convenient Preparation of Substituted 5-Amino oxazoles via a Microwave-Assisted Cornforth Rearrangement
Brad Nolt, Merck & Co.
The preparation of oxazole-4-carboxamides and their subsequent thermal rearrangement to 5-amino-oxazole-4-carboxylates is optimized in a high-speed microwave-assisted procedure. The reaction sequence is effective with a variety of substituted oxazoles, and cleanly produces products in good yield and of high purity.

Scaling-up Microwave Reactions: An Overview of the Advancer
Joe Pawluczyk, Merck & Co.
Microwave technology has opened the door to faster, cleaner and higher yielding reactions over conventional conditions. Though there are scaling limitations with current bench top instruments. This talk will present a brief overview of Biotage's Advancer along with some recent examples from our laboratory.

The Role of Microwave Assisted Chemistry in the Synthesis of Small Molecule Libraries
Stefan Werner, Ph.D., University of Pittsburgh
The University of Pittsburgh Center for Chemical Methodologies and Library Development (UPCMLD) applies methodologies that were developed in our Department to library synthesis. Microwave-assisted organic synthesis is used frequently for solution phase chemistry as well as for resin bound reagents and for scavenging techniques. It completely replaced the traditional oil bath in our laboratories. This talk will discuss the application of microwave chemistry in several mid-size solution phase small molecule libraries.