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

153 publications found for Synthetic and heterocyclic chemistry

Cover of Org. Process Res. Dev.
Graphical abstract for The Use of Gases in Flow Synthesis

Journal article

The Use of Gases in Flow Synthesis

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

Org. Process Res. Dev. · 2016 · 20 · 327–360

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineering

This review will highlight the potential benefits that can be leveraged by using flow chemistry to allow gases to be used in research in a safer and more efficient way. An overview of the different approaches used to introduce gases into flow reactors is pres…

Open DOIPDF
Cover of Chem. Eng. Technol.
Graphical abstract for A Short Multistep Flow Synthesis of a Potential Spirocyclic Fragrance Component

Journal article

A Short Multistep Flow Synthesis of a Potential Spirocyclic Fragrance Component

Baxendale, I. R.

Chem. Eng. Technol. · 2015 · 38 · 1713–1716

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

The search for novel chemical architectures displaying improved biological properties is a never-ending synthetic challenge. In this context many new test structures are often conceived by selecting and replicating specific design elements from naturally occu…

Open DOIPDF
Cover of J. Pharm. Sci.
Graphical abstract for Achieving Continuous Manufacturing: Technologies and Approaches for Synthesis, Workup, and Isolation of Drug Substance

Journal article

Achieving Continuous Manufacturing: Technologies and Approaches for Synthesis, Workup, and Isolation of Drug Substance

Baxendale, I. R.; Braatz, R. D.; Hodnett, B. K.; Jensen, K. F.; Johnson, M. D.; Sharratt, P.; Sherlock J.-P.; Florence, A. J.

J. Pharm. Sci. · 2015 · 104 · 781–791

Synthetic and heterocyclic chemistryRoute design and process chemistry

This whitepaper highlights current challenges and opportunities associated with continuous synthesis, workup, and crystallization of active pharmaceutical ingredients (drug substances). We describe the technologies and requirements at each stage and emphasize…

Open DOIPDF
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 Molbank
Graphical abstract for Ethyl 2-hydroxy-2-phenyl-2-(thiazol-2-yl)acetate

Journal article

Ethyl 2-hydroxy-2-phenyl-2-(thiazol-2-yl)acetate

Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R.

Molbank · 2015 · 2015(1) · M857

Synthetic and heterocyclic chemistry

This short note describes the synthesis of the title compound through spontaneous aerobic oxidation of ethyl 2-phenyl-2-(thiazol-2-yl)acetate. Due to the prevalence of such functional motifs in biologically active substances, we believe the oxidation encounte…

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…

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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 Molbank
Graphical abstract for Syn-Ethyl 1-hydroxy-7-methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinolone-3-carboxylate HCl Salt

Journal article

Syn-Ethyl 1-hydroxy-7-methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinolone-3-carboxylate HCl Salt

Baumann, M.; Baxendale, I. R.

Molbank · 2015 · 1 · M846

Synthetic and heterocyclic chemistry

This short note describes a one-step synthesis of the title compound from commercially available starting materials and reports its full spectroscopic characterization data.

Open DOIPDF
Cover of J. Org. Chem.
Graphical abstract for Synthesis of 1,3,6-Trisubstituted Azulenes

Journal article

Synthesis of 1,3,6-Trisubstituted Azulenes

Leino, T. O.; Baumann, M.; Yli-Kauhaluoma, J. Baxendale, I. R.; Wallén, E. A. A.

J. Org. Chem. · 2015 · 80 · 11513–11520

Synthetic and heterocyclic chemistry

We have developed a short, general synthetic route to 1,3,6-trisubstituted azulenes. The key intermediate, 6-methylazulene, was synthesized from readily available and inexpensive starting materials in 63% yield over two steps. The methyl group of 6-methylazul…

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 Beilstein J. Org. Chem.
Graphical abstract for Thiazole Formation Through a Modified Gewald Reaction

Journal article

Thiazole Formation Through a Modified Gewald Reaction

Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R.

Beilstein J. Org. Chem. · 2015 · 11 · 875–883

Synthetic and heterocyclic chemistry

The synthesis of thiazoles and thiophenes starting from nitriles, through a modified Gewald reaction has been studied for a number of different substrates. 1,4-dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-su…

Open DOIPDF