Myriad Multiplicity in Nitroenamine Multicomponent Methodology

Posted on behalf of Jennifer Lee, guest web writer for Organic & Biomolecular Chemistry

Not many molecules can claim to be both a Michael donor and Michael acceptor while containing a good leaving group as is the case with nitroketene-N,S-acetals like N-methyl-S-methyl nitroethylene (NMSM), broadly categorized as nitroenamines.

As a double actor in the pseudo three-component reaction investigated by Rao and Parthiban, moieties of NMSM react three times in two roles:  twice as a nucleophile and once as an electrophile.  The other components in the same pot included the aromatic aldehyde and catalytic 2-aminopyridine.

The methodology generates an alternate route from the classic Hantzsch reaction to the 1,4-dihydropyridine (DHP) platform with a broader scope and purification by recrystallization.  Advantageously, 1,4-DHPs are calcium channel blockers and hydride sources for reduction.

The functionally-rich NMSM component conveniently diversifies DHP which could lead to more potent medicinal applications or pesticides.

The two inherent diversity points on the platform arose from the aldehyde and amine precursors.  Additional diversity from amine substitution of the built-in sulfide leaving group created a total of 29 unique 1,4-DHP possibilities.

Specifically, they synthesized a neonictinoid insecticide analogue to the popular nitenpyram compound to constrain the alkene to the cis-isomer with muted toxicity to mammals.

Overall, leveraging an electronically versatile synthon like NMSM in a multicomponent reaction leads to enhanced diversity for analoging with myriad compounds that could perform better than those currently available.

To find out more see:

One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines
H. Surya Prakash Rao and A. Parthiban
DOI: 10.1039/c4ob00628c

Jennifer LeeJennifer Lee is currently a Ph.D. candidate in Dr. George Kraus’ organic chemistry lab at Iowa State University.  Her research focuses on designing methodologies to transform carbohydrate-derived biomass into biorenewable commodity and specialty chemicals.  The creation of a versatile platform technology led to diverse and industrially-relevant aromatic compounds to work toward a more sustainable future.

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Vaccines for heroin

Arun Ankush Tanpure, a graduate student at IISER Pune, India, writes on a recent OBC article

The number of deaths due to heroin overdoses has severely increased in last decade, and regular consumption of heroin leads to serious health concerns.

Vaccination is one of the emerging choices among heroin rehabilitation therapies. In general, these vaccines contain heroin-like hapten as a pharmacophore that acts as an antagonist. This antagonist has high affinity for heroin receptors but does not activate them, hence reverses the effects of heroin. Because of inherent chemical instability, when entered in to bloodstream these anti-heroin drugs rapidly metabolise into several by-products, which makes development of effective vaccines against heroin particularly challenging.

Recently an American research group at National Institute on Drug Abuse (NIDA) lead by Professor Kenner Rice has reported the synthesis and immunological evaluation for a series of haptens.

The team has emphasised the hydrolytic stability of hapten scaffolds and envisioned that hapten with amido groups at both the C3 and C6 positions should be more stable than a hapten with an ester in one of those positions. Insertion of a 3-amino group and the construction of a C-6α-(2-oxo-propyl) group stereoselectively was the challenging task towards the synthesis of designed hapten derivatives. The group has tackled the synthetic hurdle by adopting convergent synthesis approach and validating the stereochemistry by single X ray crystallography.

Furthermore, in vivo Immunological studies of all three new synthetic haptens reveals that one derivative DiAmHap (3) is chemically more stable and better candidate for a heroin vaccine than 6-PrOxyHap (1) and DiPrOxyHap (2). This work is a very positive step towards the development of vaccines for heroin abuse.

Synthesis and immunological effects of heroin vaccines
Fuying Li, Kejun Cheng,  Joshua F. G. Antoline, Malliga R. Iyer, Gary R. Matyas, Oscar B. Torres, Rashmi Jalah, Zoltan Beck, Carl R. Alving, Damon A. Parrish, Jeffrey R. Deschamps, Arthur E. Jacobson and Kenner C. Rice
DOI: 10.1039/C4OB01053A

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Amino acids: fluorescensors for mercury ions

Arun Ankush Tanpure, a graduate student at IISER Pune, India, writes on a recent OBC article

Many human activities have been responsible for heavy metal poisoning in recent years, Mercury (Hg) poisoning being one of them. Mercury occurs in several forms and even trace concentrations of mercury ions in crops, fish or the human body are enough to produce potentially toxic effects to vital organs. Mercury poisoning can lead to several diseases including Acrodynia (also known as the pink disease), the Hunter-Russell syndrome and the Minamata disease.

Selective detection of mercury, particularly in aqueous media, has been a key area for analytical chemists, since traditional analytical techniques for mercury detection are time consuming, laborious and involve expensive instrumentation. In this work, Korean researcher Keun-Hyeung Lee and co-workers have developed a pair of very sensitive amino acid based fluorescence-ON probes for the exclusive detection of mercury ions in aqueous solution.

The team has combined the fluorescence properties of pyrene and Hg(II) binding ability of tyrosine residues for the design and synthesis of two novel fluorescensors. Both newly-synthesised probes show emission maxima at 386 and 400 nm in the absence of Hg(II) ion. Upon titration with Hg(II) ions, both probes show exponential fluorescence enhancement and display a remarkable red shift (90-100 nm) emission. These probes are also highly selective for mercury ions in the presence of a range of other metal ions and are effective in aqueous solutions.

The team further clarifies the binding mode of these sensors and the coordination of the metal ion. This method can be implemented for rapid and quantitative detection of Hg(II) from various polluted water sources. This work also underscores the unconventional use of an amino acid as a chemosensor.

Ratiometric fluorescence chemosensor based on tyrosine derivatives for monitoring mercury ions in aqueous solutions
Ponnaboina Thirupathi, Ponnaboina Saritha (née Gudellin) and Keun-Hyeung Lee
DOI: 10.1039/C4OB01044B

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Recent HOT Organic & Biomolecular Chemistry articles

Check out the following HOT articles, these have been made free to access for a limited time:

Synthesis and immunological effects of heroin vaccines
Fuying Li, Kejun Cheng, Joshua F. G. Antoline, Malliga R. Iyer, Gary R. Matyas, Oscar B. Torres, Rashmi Jalah, Zoltan Beck, Carl R. Alving, Damon A. Parrish, Jeffrey R. Deschamps, Arthur E. Jacobson and Kenner C. Rice
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Synthesis and immunological effects of heroin vaccines

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6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures
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Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactions
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New reagents for detecting free radicals and oxidative stress

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14th Anglo-Italian Meeting on Heterocyclic Chemistry

The 14th Anglo-Italian Meeting on Heterocyclic Chemistry, organised by the Heterocyclic & Synthesis Group in collaboration with the Italian Chemical Society, recently took place.

14th Anglo-Italian Meeting on Heterocyclic Chemistry conference photo 2014

It was an excellent meeting, held at Cumberland Lodge in Windsor Great Park, with around 50 participants, equally split between the two countries. There were some excellent lectures, including plenaries from:

  • Professor Stephen Clark (University of Glasgow)
  • Professor Sabine Flitsch (University of Manchester)
  • Dr King Kuok (Mimi) Hii (Imperial College London)
  • Professor Emanuela Licandro (University of Milan)
  • Professor Andrea Pace (University of Palermo)
  • Professor Claudio Trombini (University of Bologna)

Our congratulations go to  Susan Lepri from University of Perugia who won our poster prize.

Susan receiving her prize from Professor Chris Willis (Heterocyclic Group) and Professor Giuseppe Musumarra (Italian Chemical Society)

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HOT OBC articles updated throughout the month…

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Lara Cala, Francisco J. Fañanás and Félix Rodríguez  
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Jeffrey Buter, Renée Moezelaar and Adriaan J. Minnaard  
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RSC Organic Division Poster Symposium 2014

RSC Organic Division Poster Symposium 2014, headline sponsored by F. Hoffmann-La Roche, Ltd.

The poster symposium, for final year organic chemistry PhD students, will take place at The Royal Society of Chemistry, Burlington House, London on Monday 01 December 2014.

The symposium offers final year PhD students a chance to showcase their research to their peers, leading academics and industrial chemists, and is open to all branches of organic chemistry. The symposium has a tradition of being the most competitive and highly regarded organic chemistry symposium for PhD students in the UK and ROI and we would like to thank F. Hoffmann-La Roche, Ltd. for their generous support of the event.

There will be a first prize of £500, two runner-up prizes of £250, and a “selected by Industry Prize”. Industrial delegates will make this selection by considering the research’s potential for application in an industrial context; the winner will also receive a prize of £500.

Closing date for submissions is Wednesday 01 October 2014.
For more information and to submit your abstract go to http://rsc.li/organic-poster

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When a Spectator is not Just a Spectator in Iodonium Salts

Advances in hypervalent iodine are flourishing1 from the classic non-toxic Dess-Martin periodinane oxidation to synthetic reagents for elaborate natural products2. New types of both iodine(III) and iodine(V) compounds are constantly being discovered for ever increasing applications.

Iodonium salts, classified as iodine(III) compounds, are notoriously electrophilic. Those with two carbon ligands like alkynyl(aryl)iodonium salts react with a nucleophile which couples with the alkyne.  Overall, the reaction seemingly pieces together two nucleophilic entities.

The remaining aryl iodide in the balanced equation seems to be a “spectator” since it is absent in the product, but in this recent (open access) paper Hamnett and Moran sought to investigate whether that is truly the case.

They improved the preparation of alkynyl(aryl)iodonium tosylates and systematically applied them to two model reactions, finding that the 2-anisyl ligand provided the highest yields.

It significantly out-performed the 3-anisyl derivative, suggesting that the key to success is the inherent stability of the 2-anisyl iodonium salt with the methoxy group ideally situated for coordination to the iodine.

Discovering the effectiveness of the 2-anisyl ligand in iodonium salts could have implications for more efficient transformations involving hypervalent iodine.  More broadly, the work shows the importance of optimizing reactions across all variables and highlighting that spectators may not always be simple bystanders.

To find out more see:

Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group
David J. Hamnett and Wesley J. Moran
DOI: 10.1039/C4OB00556B


1. M. S. Yusubov, A. V. Maskaev and V. V. Zhdankin, ARKIVOC, 2011, i, 370–409.
2. D. J. Wardrop and J. Fritz, Org. Lett., 2006, 8, 3659–3662.

Posted on behalf of Jennifer Lee, guest web writer for Organic & Biomolecular Chemistry

Jennifer LeeJennifer Lee is currently a Ph.D. candidate in Dr. George Kraus’ organic chemistry lab at Iowa State University. Her research focuses on designing methodologies to transform carbohydrate-derived biomass into biorenewable commodity and specialty chemicals. The creation of a versatile platform technology led to diverse and industrially-relevant aromatic compounds to work toward a more sustainable future.

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OBC Poster Prize winner at ISMSC-9 in Shanghai

Congratulations to Hanna Jędrzejewska from the Polish Academy of Sciences in Warsaw for winning the Organic & Biomolecular Chemistry poster prize awarded at the 9th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC-9) held at SIOC, Shanghai, on 7-11 June 2014.

The title of her winning poster was: Chiral self-sorting of hybrid peptidic capsules

Hanna wins a copy of the book Polymeric and Self Assembled Hydrogels : From Fundamental Understanding to Applications, signed by its author, and winner of the 2014 Cram Lehn Pedersen Prize Prof. Oren Scherman.

Hanna Jędrzejewska, OBC Poster Prize winner (right) is presented with a certificate and RSC Book, by Prof. Andrew Wilson (left) and Dr. Marie Cote (OBC Deputy Editor, centre)

On her winning work, Hanna comments:

This project aims at the synthesis of bio-compatible peptidic capsules by means of self-organization of short peptides. Such capsules can be further used for encapsulation, storage and transport of biologically relevant targets. Even though peptides are endowed with natural self-assembling properties, capsules made of short “native” peptides do not form spontaneously due to high conformational lability and tendency to form non-porous random aggregates. I have found that this disadvantage can be overcome by properly designed scaffolds that “guide” peptides into capsular structures. I have used short peptides of various chirality attached in a dynamical covalent way to the macrocyclic skeleton. This way I have obtained building blocks that spontaneously self-sort into porous peptidic capsules resembling closed β-barrels.

I’ve been working on this topic for 1 year. This research is fully supported by the PARENT/BRIDGE programme that enables the best researchers who are raising young children to return to advanced research work. The programme is financed by Foundation for Polish Science within European Regional Development Fund under the Innovative Economy Operational Programme 2007-2013.

Hanna works as a PhD student in the group of Prof. Agnieszka Szumna.

Congratulations again to Hanna – the OBC team whishes her all the very best with her research work!

From left to right: Prof. Zhanting Li, Hanna Jędrzejewska (OBC Poster Prize Winner), Prof. Andrew Wilson, Prof. Oren Scherman, Dr. Robert Eagling, Prof. Jonathan Sessler and Dr Marie Cote

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