Baxendale GroupAdvanced synthetic chemistry, engineered for scaleDepartment of Chemistry

Research record

Publications

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Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringAutomation and analyticsPhotochemistryHazardous and reactive intermediatesImmobilised reagents and scavengers

53 publications found for Route design and process chemistry

Cover of J. Org. Chem.
Graphical abstract for Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade

Journal article

Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade

Baumann, M.; Baxendale, I. R.

J. Org. Chem. · 2015 · 80 · 10806–10816

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

An efficient reaction cascade delivering a series of pyrrolo[1,2-a]quinolines bearing phosphonate or phosphine oxide moieties is presented. This sequence exploits the in situ transformation of propargylic alcohols into transient allenes by means of a strategi…

Open DOIPDF
Cover of Euro. J. Med. Chem.
Graphical abstract for Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Journal article

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Christodoulou, M. S.; Calogero, F.; Baumann, M.; García-Argáez, A. N.; Pieraccini, S.; Sironi, M.; Dapiaggi, F.; Bucci, R.; Broggini, G.; Gazzola, S.; Liekens, S.; Silvani, A.; Lahtela-Kakkonen, M.; Martinet, N.; Nonel-Canals, A.; Santamaría-Navarroh, E.; Baxendale, I. R.; Via, L. D.; Passarell, D.

Euro. J. Med. Chem. · 2015 · 92 · 766–775

Synthetic and heterocyclic chemistryRoute design and process chemistry

Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The anti-p…

Open DOIPDF
Cover of Org. Biomol. Chem.
Graphical abstract for Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines

Journal article

Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines

Baumann, M.; Rodriguez Garcia, A. M.; Baxendale, I. R.

Org. Biomol. Chem. · 2015 · 13 · 4231–4239

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineering

The efficient flow synthesis of important heterocyclic building blocks based on the 1,2,4-triazole and pyrrolo[1,2-c]pyrimidine scaffold has been achieved. Crucially, a telescoped continuous flow process was developed based on the reaction of N-formylglycin…

Open DOI
Cover of Eur. J. Org. Chem.
Graphical abstract for Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

Journal article

Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

Stanetty, C.; Baxendale, I. R.

Eur. J. Org. Chem. · 2015 · 12 · 2718–2726

Synthetic and heterocyclic chemistryRoute design and process chemistry

The higher-carbon sugar L-glycero-D-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addre…

Open DOIPDF
Cover of Beilstein J. Org. Chem.
Graphical abstract for The synthesis of active pharmaceutical ingredients (APIs)using continuous flow chemistry

Journal article

The synthesis of active pharmaceutical ingredients (APIs)using continuous flow chemistry

Baumann, M.; Baxendale, I. R.

Beilstein J. Org. Chem. · 2015 · 11 · 1194–1219

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringAutomation and analytics

The implementation of continuous flow processing as a key enabling technology has transformed the way we conduct chemistry and has expanded our synthetic capabilities. As a result many new preparative routes have been designed towards commercially relevant …

Open DOIPDF
Cover of Molecules
Graphical abstract for Synthesis of Riboflavines, Quinoxalinones and Benzodiazepines through Chemoselective Flow Based Hydrogenations

Journal article

Synthesis of Riboflavines, Quinoxalinones and Benzodiazepines through Chemoselective Flow Based Hydrogenations

Baumann M.; Baxendale, I. R.; Hornung, C. H.; Ley, S. V.; Rojo, M. V.; Roper, K. A.

Molecules · 2014 · 19 · 9736–9759

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

Robust chemical routes towards valuable bioactive entities such as riboflavines, quinoxalinones and benzodiazepines are described. These make use of modern flow hydrogenation protocols enabling the chemoselective reduction of nitro group containing building b…

Open DOIPDF
Cover of Green Process Synth.
Graphical abstract for Flow chemistry approaches directed at improving chemical synthesis

Journal article

Flow chemistry approaches directed at improving chemical synthesis

Baxendale, I. R.; Mallia, C. J.; Brocken, L.

Green Process Synth. · 2013 · 2 · 211–230

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineering

Flow synthesis offers many advantages when applied to the processing of difficult or dangerous chemical transformations. Furthermore, continuous production allows for rapid scale up of reactions without significant redevelopment of the routes. Importantly, it…

Open DOIPDF
Cover of A.C.S. Med. Chem. Lett.
Graphical abstract for Flow Synthesis and Bio-Pharmacological Studies of a P2X7 Antagonist that Shows Analgesic Activity

Journal article

Flow Synthesis and Bio-Pharmacological Studies of a P2X7 Antagonist that Shows Analgesic Activity

Battilocchio, C.; Guetzoyan, L.; Cervetto, C.; Mannelli, L. D. C.; Daniela Frattaroli, D.; Baxendale, I. R.; Maura, G.; Sautebin, L.; Biava, M.; Ghelardini, C.; Marcoli, M.; Ley, S. V.

A.C.S. Med. Chem. Lett. · 2013 · 4(8) · 704–709

Synthetic and heterocyclic chemistryRoute design and process chemistry

We report the biological evaluation of a class of adamantane derivatives, which were achieved via modified telescoped machine-assisted flow procedure. Among the series of compounds tested in this work, 5 demonstrated outstanding analgesic properties. This co…

Open DOIPDF
Cover of Beilstein J. Org. Chem.
Graphical abstract for The rapid generation of isothiocyanates in flow

Journal article

The rapid generation of isothiocyanates in flow

Baumann, M.; Baxendale, I. R.

Beilstein J. Org. Chem. · 2013 · 9 · 1613–1619

Route design and process chemistryImmobilised reagents and scavengers

Isothiocyanates are versatile starting materials for a wide range of chemical reactions. However, their high nucleophilic susceptibility means they are best prepared and used immediately. We report here on a flow platform for the fast and efficient formatio…

Open DOIPDF
Cover of Chem. Eur. J.
Graphical abstract for Establishing a flow process to coumarin-8-carbaldehydes as important synthetic scaffolds

Journal article

Establishing a flow process to coumarin-8-carbaldehydes as important synthetic scaffolds

Zak, J.; Ron, D.; Riva, E.; Harding, H. P.; Cross, B. C. S.; Baxendale, I. R.

Chem. Eur. J. · 2012 · 32 · 9901–9910

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineering

Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin-8-carbaldehydes are lacking. We describe here a high-yielding continuous flow synthesis that requires no manual intermediate purification or work-up, …

Open DOIPDF
Cover of Synthesis
Graphical abstract for Flow Assisted Scale-up of C2-symmetric Chiral PyBox-Ligands

Journal article

Flow Assisted Scale-up of C2-symmetric Chiral PyBox-Ligands

Battilocchio, C.; Baumann, M.; Baxendale, I. R.; Biava, M.; Kitching, M. O.; Ley, S. V.; Martin, R. E.; Ohnmacht, S. A.; Tappin, N. D. C.

Synthesis · 2012 · (4) · 635–647

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineering

A series of PyBox ligands were prepared from commercially available chelidonic acid by a multistep flow sequence using mesoreactor technology. A chloro group introduced onto the ligand scaffold was subsequently exploited to give amine derivatives ready for im…

Open DOIPDF
Cover of Aust. J. Chem.
Graphical abstract for Flow Microwave Technology and Microreactors in Synthesis

Journal article

Flow Microwave Technology and Microreactors in Synthesis

Baxendale, I. R.; Hornung, C.; Ley, S. V.; Munõz Molina, J. de M.; Wikstrom, A.

Aust. J. Chem. · 2012 · 66 · 131–144

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineering

A bespoke microwave reactor with a glass containment cell has been developed for performing continuous flow reactions under microwave heating. The prototype unit has been evaluated using a series of standard organic chemical transformations enabling scale-up …

Open DOIPDF