Baxendale GroupAdvanced synthetic chemistry, engineered for scaleDepartment of Chemistry

Research record

Publications

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201 publications found

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

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

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…

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Cover of Chem. Eng. Tech.
Graphical abstract for Back Pressure Regulation of Slurry Forming Reactions in Continuous FlowGraphical abstract unavailable

Journal article

Back Pressure Regulation of Slurry Forming Reactions in Continuous Flow

Deadman, B. J.; Ley, S. V.; Browne, D. L.; Baxendale, I. R.

Chem. Eng. Tech. · 2015 · 38 · 259–264

The handling of solid components in flow chemical processes is still a significant challenge. Current devices for regulating back pressure in laboratory-scale flow chemistry experiments are vulnerable to blockage by solid particulates. A simple device is pres…

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

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

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…

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Cover of Euro. J. Med. Chem.
Graphical abstract for Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2Graphical abstract unavailable

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

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…

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Cover of Molbank
Graphical abstract for Ethyl 2-hydroxy-2-phenyl-2-(thiazol-2-yl)acetateGraphical abstract unavailable

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

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…

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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]pyrimidinesGraphical abstract unavailable

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

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-heptopyranoseGraphical abstract unavailable

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

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…

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

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

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

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Cover of J. Org. Chem.
Graphical abstract for Synthesis of 1,3,6-Trisubstituted AzulenesGraphical abstract unavailable

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

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…

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

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

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 …

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Cover of Beilstein J. Org. Chem.
Graphical abstract for Thiazole Formation Through a Modified Gewald ReactionGraphical abstract unavailable

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

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…

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Cover of Org. Biomol. Chem.
Graphical abstract for Total syntheses of natural products containing spirocarbocyclesGraphical abstract unavailable

Journal article

Total syntheses of natural products containing spirocarbocycles

Smith, L. K.; Baxendale, I. R.

Org. Biomol. Chem. · 2015 · 13 · 9907–9933

The structures of natural products from a variety of sources contain spirocycles, two rings that share a common atom. The spiro motif is finding increasing inclusion in drug candidates, and as a structural component in several promising classes of chiral liga…

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