Heterocyclic Chemistry

Heterocyclic Chemistry

by Roger Read

Australia was pleased to host the biennial International Congress for Heterocyclic Chemistry (ICHC21), 15–20 July 2007, for the first time in the history of the Congress. It attracted well over 400 delegates from more than 40 countries. As always, the standard of the conference was high, due to the quality of the plenary, award, and keynote lectures, and the many stimulating contributed papers that were presented in oral and poster form across the full range of topics in heterocyclic chemistry.

Professor Margaret Brimble, president of the ISHC, speaking at the opening ceremony.

The Venue

The venue, at the University of New South Wales (UNSW), close to the center of Sydney, provided an attractive, modern academic backdrop to the conference. The university provided convenient access to coastal beach scenery and lively attractions in and around Sydney Harbor and Darling Harbor. The Congress was organized under the auspices of the International Society for Heterocyclic Chemistry and a local committee headed by David Black. The program, ably coordinated by Kate Jolliffe (University of Sydney), was designed to bring together heterocyclic chemists from industry and government research laboratories, as well as academia, and care was taken to engage and showcase local industry.

The Opening

Delegates and guests were welcomed by Margaret Brimble (University of Auckland), president of the ISHC. The Congress was officially opened by the New South Wales Governor, Her Excellency Professor Marie Bashir, who spoke of the importance of heterocycles as drug candidates, bioactive materials, and chemicals that had played major roles in agriculture and the pharmaceutical industry. She also praised the many important advances in fundamental science and applied technology that had resulted from the study of heterocyclic compounds and their chemistry.

The Program

With his lecture on cycloaddition reactions of 2-azoniaheterodienes, professor Scott Denmark (University of Illinois) then set the scene for what was to be a week-long feast of formal scientific presentations, including two poster sessions, a trade exhibition, and informal networking.

New cycloaddition and annulation strategies were revisited later in the conference through lectures by Rick Danheiser (Massachusetts Institute of Technology), Shengming Ma (Shanghai Institute of Organic Chemistry) and Andrew Holmes (University of Melbourne), who adopted them for synthesis of a range of heterocycles of biological interest. Ferenc Fülöp (University of Szeged) also gave an overview of his contributions toward understanding the ring chain equilibrium of 1,3-(X-N)-heterocycles.

There followed expositions of new synthetic methods to unusual classes of heterocycles, such as silole heterocycles, by Masahiro Murakami (Kyoto University), and a fascinating study by Alan Rowan (University of Nijmegen) of polymer threading mechanisms that have found importance in the development of processive rotaxane catalysts. The topic of catalysis and the design of new catalysts and catalytic processes was picked up later in the conference, particularly around the lecture on chiral phenyl-bis(oxazoline) derivatives in asymmetric catalysis by Hisao Nishayama (Nagoya University).

The relevance of new technologies, such as microwave acceleration, in heterocyclic chemistry was summarized in a series of presentations by pioneers of the field, Rajendar Varma (U.S. Environmental Protection Agency) and Nicholas Leadbeater (University of Connecticut), and put into practical context by Keller Barnhardt (CEM Corporation). The power of programmed self-assembly in providing new heterocycle-based materials for molecular electronic and optoelectronic applications and opportunities in functional nanomaterials was beautifully presented by Takuzo Aida (University of Tokyo) and Thomas Carell (University of Munich).

Presentation of congress plaque by Professor Girolamo Cirrincione, chair of ICHC20, to Professors David Black and Roger Read, co-chairs of ICHC21.

Others, including Toshiaki Mase (Banyu Pharmaceutical Company), David Tschaen (Merck USA), and Naresh Kumar (UNSW), provided updates on the establishment of commercially viable synthetic chemistry in support of the use of biologically active heterocyclic molecules for drug development. Presenters on these topics described the discovery and adoption of natural products and natural product analogues in the development process, and efforts to harness supramolecular chemistry of heterocyclic derivatives, including those of Troger’s base and novel macrocyclic systems, to develop functional and diagnostic materials. Efforts to understand and mimic natural heterocyclic systems provided another theme of enquiry in de novo and biological control studies, and this topic was developed by Cynthia Burrows (University of Utah) in her lecture on guanine oxidation in genomic and mitochondrial DNA. Such oxidative damage leads to hydantoin products by previously unrecognized pathways.

Total synthesis and improvements in existing synthetic methods were featured in much of the work described, but plenary lectures in this area included the work of Mikiko Sodeoka (RIKEN Institute of Physical and Chemical Research) on enantioselective synthesis of heterocycles based on palladium enolate chemistry, the underlying methods developed by Thorsten Bach (Technical University Munich) for the total synthesis of heterocyclic natural products, and the design and synthesis of heterocyclic cleft-shaped receptors for molecular recognition and transport (Phillip Gale, University of Southampton).

Awards for Heterocyclic Chemistry

Other scientific highlights of the program included the presentations of the ISHC Senior Prize in Heterocyclic Chemistry (sponsored by Pfizer) to Professor K.C. Nicolaou (Scripps Research Institute), and the ISHC Katritzky Junior Award in Heterocyclic Chemistry to Professor David MacMillan (Princeton University), respectively. Each gave marvelous award lectures that illustrated the power and elegance of their discrete areas of heterocyclic chemistry and reinforced the outstanding contributions that they have made to modern heterocyclic chemistry, especially in the areas of targeted synthesis and generally applicable synthetic methods.

The organizers were thankful to have the support of the Australian heterocyclic chemistry community and local sponsors and exhibitors, including the New South Wales Department of State and Regional Development, who ensured the viability of the meeting. But no conference can be a success without the delegates, some of whom had come from the far side of the globe, and with some hardship. We recommend attendance at the next ICHC, which will be held in St John’s, Newfoundland, August 2009.

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