Professor Ian Baxendale's Outputs (196)

2,4,6-Trichloro-cyclohexa-2,5-dienone (2025)
Journal Article
Gambacorta, G., Teo, Q. H., & Baxendale, I. R. (2025). 2,4,6-Trichloro-cyclohexa-2,5-dienone. Molbank, 2025(1), Article M1969. https://doi.org/10.3390/m1969

A continuous flow process was optimised for the perchlorination of p-cresol to the corresponding 2,4,6-trichloro-cyclohexa-2,5-dienone derivative employing trichloroisocyanuric acid as a green and safer-to-handle chlorinating agent. The system could... Read More about 2,4,6-Trichloro-cyclohexa-2,5-dienone.

Discovery of a Potent Dual Inhibitor of Aromatase and Aldosterone Synthase. (2023)
Journal Article
Tinivella, A., Banchi, M., Gambacorta, G., Borghi, F., Orlandi, P., Baxendale, I. R., …Rastelli, G. (2023). Discovery of a Potent Dual Inhibitor of Aromatase and Aldosterone Synthase. ACS pharmacology & translational science, 6(12), 1870-1883. https://doi.org/10.1021/acsptsci.3c00183

Estrogen deficiency derived from inhibition of estrogen biosynthesis is a typical condition of postmenopausal women and breast cancer (BCs) patients undergoing antihormone therapy. The ensuing increase in aldosterone levels is considered to be the ma... Read More about Discovery of a Potent Dual Inhibitor of Aromatase and Aldosterone Synthase..

Spectroscopic dataset of Hedione's derivatives gathered during process development (2022)
Journal Article
Sharley, J. S., Gambacorta, G., Pérez, A. M. C., Ferri, E. E., Miranda, A. F., Quesada, J. S., & Baxendale, I. R. (2023). Spectroscopic dataset of Hedione's derivatives gathered during process development. Data in Brief, 46, https://doi.org/10.1016/j.dib.2022.108801

The dataset of spectroscopic analysis performed on starting materials, intermediates, and products relating to the synthesis of Hedione are hereby presented. The data were acquired in Durham university during the period between October 2020 and Septe... Read More about Spectroscopic dataset of Hedione's derivatives gathered during process development.

A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione (2022)
Journal Article
Sharley, J. S., Gambacorta, G., Collado Pérez, A. M., Ferri, E. E., Miranda, A. F., Fernández, I. F., Quesada, J. S., & Baxendale, I. R. (2022). A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione. Tetrahedron, 126, https://doi.org/10.1016/j.tet.2022.133068

A new method for the oxidation of Hedione 1 to dehydrohedione 2, a high value intermediate in the flavour and fragrance industry, has developed based upon one pot α-chlorination-elimination sequence which can be readily scaled. The spontaneous elimin... Read More about A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione.

Further investigations into imine-mediated formation of allylic nitro compounds (2022)
Journal Article
Sharley, J. S., Gambacorta, G., Collado Pérez, A. M., Ferri, E. E., Miranda, A. F., Quesada, J. S., & Baxendale, I. R. (2022). Further investigations into imine-mediated formation of allylic nitro compounds. Tetrahedron, 126, https://doi.org/10.1016/j.tet.2022.133058

Nitro alkanes are valuable starting materials for functionalisation via their corresponding anions as well as their transformation into other important groups such as ketones via the Nef reaction. Herein, we report a process development study for the... Read More about Further investigations into imine-mediated formation of allylic nitro compounds.

Identification of potential biological targets of oxindole scaffolds via in silico repositioning strategies (2022)
Journal Article
Tinivella, A., Pinzi, L., Gambacorta, G., Baxendale, I., & Rastelli, G. (2022). Identification of potential biological targets of oxindole scaffolds via in silico repositioning strategies. F1000Research, 11, https://doi.org/10.12688/f1000research.109017.2

Background: Drug repurposing is an alternative strategy to traditional drug discovery that aims at predicting new uses for already existing drugs or clinical candidates. Drug repurposing has many advantages over traditional drug development, such as... Read More about Identification of potential biological targets of oxindole scaffolds via in silico repositioning strategies.

Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone (2022)
Journal Article
Gambacorta, G., & Baxendale, I. R. (2022). Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone. Organic Process Research and Development, 26, 422-430. https://doi.org/10.1021/acs.oprd.1c00440

A continuous-flow preparation of 2-benzoxazolinone via the Hofmann rearrangement of salicylamide has been implemented employing trichloroisocyanuric acid as the stable and atom-economic chlorinating agent. The system was optimized to avoid solid accu... Read More about Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone.

6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride (2022)
Journal Article
Nicholls, A. J., & Baxendale, I. R. (2022). 6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride. Molbank, 2022(1), Article M1339. https://doi.org/10.3390/m1339

This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medici... Read More about 6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride.

4,4’-(Pyridin-4-ylmethylene)dibenzonitrile (2021)
Journal Article
Lancaster, B. M., Nicholls, A. J., & Baxendale, I. R. (2021). 4,4’-(Pyridin-4-ylmethylene)dibenzonitrile. Molbank, 2021(4), Article M1302. https://doi.org/10.3390/m1302

This communication describes an unprecedented substitution cascade, in which 4-methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual SNAr process, to form a novel triarylmethane structure. A proposed mecha... Read More about 4,4’-(Pyridin-4-ylmethylene)dibenzonitrile.

Protein domain-based prediction of drug/compound–target interactions and experimental validation on LIM kinases (2021)
Journal Article
Doğan, T., Akhan Güzelcan, E., Baumann, M., Koyas, A., Atas, H., Baxendale, I. R., Martin, M., & Cetin-Atalay, R. (2021). Protein domain-based prediction of drug/compound–target interactions and experimental validation on LIM kinases. PLoS Computational Biology, 17(11), Article e1009171. https://doi.org/10.1371/journal.pcbi.1009171

Predictive approaches such as virtual screening have been used in drug discovery with the objective of reducing developmental time and costs. Current machine learning and network-based approaches have issues related to generalization, usability, or m... Read More about Protein domain-based prediction of drug/compound–target interactions and experimental validation on LIM kinases.

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents (2021)
Journal Article
Murie, V. E., Nicolino, P. V., dos Santos, T., Gambacorta, G., Nishimura, R. H., Perovani, I. S., Furtado, L. C., Costa-Lotufo, L. V., Moraes de Oliveira, A., Vessecchi, R., Baxendale, I. R., & Clososki, G. C. (2021). Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents. Journal of Organic Chemistry, 86(19), 13402-13419. https://doi.org/10.1021/acs.joc.1c01521

We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium inte... Read More about Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents.

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries (2021)
Journal Article
Gambacorta, G., Sharley, J. S., & Baxendale, I. R. (2021). A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries. Beilstein Journal of Organic Chemistry, 17, 1181-1312. https://doi.org/10.3762/bjoc.17.90

Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlig... Read More about A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries.

Photochemical Flow Oximation of Alkanes (2020)
Journal Article
Baxendale, I. R., Griffiths, O. M., & Ruggeri, M. (2020). Photochemical Flow Oximation of Alkanes. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 31(19), 1907-1912. https://doi.org/10.1055/s-0040-1707281

The nitrosation of several alkanes using tert-butyl nitrite has been performed in flow showing a remarkable reduction in the reaction time compared with batch processing. Due to the necessity for large excesses of the alkane component a continuous re... Read More about Photochemical Flow Oximation of Alkanes.

Straight Forward and Versatile Differentiation of the l-glycero and d-glycero-d-manno Heptose Scaffold (2020)
Journal Article
Suster, C., Baxendale, I. R., Mihovilovic, M. D., & Stanetty, C. (2020). Straight Forward and Versatile Differentiation of the l-glycero and d-glycero-d-manno Heptose Scaffold. Frontiers in Chemistry, 8, Article 625. https://doi.org/10.3389/fchem.2020.00625

Bacterial lipopolysaccharides (LPS) are important bio-medical structures, playing a major role in the interaction with human immune systems. Their core regions, containing multiple units of L-glycero-D-manno heptoses (L,D-heptose), are highly conserv... Read More about Straight Forward and Versatile Differentiation of the l-glycero and d-glycero-d-manno Heptose Scaffold.

A rearrangement of 3-hydroxyazetidines into 2-oxazolines (2020)
Journal Article
Ruggeri, M., Dombrowski, A. W., Djuric, S. W., & Baxendale, I. R. (2020). A rearrangement of 3-hydroxyazetidines into 2-oxazolines. Journal of Organic Chemistry, 85(11), 7276-7286. https://doi.org/10.1021/acs.joc.0c00656

A novel rearrangement sequence of 3-hydroxyazetidines via a Ritter initiated cascade provides highly substituted 2-oxazolines in high yields. The reaction conditions and substrate scope of the transformation have been studied demonstrating the genera... Read More about A rearrangement of 3-hydroxyazetidines into 2-oxazolines.

A One-Pot Divergent Sequence to Pyrazole and Quinoline Derivatives (2020)
Journal Article
Gambacorta, G., Apperley, D. C., & Baxendale, I. R. (2020). A One-Pot Divergent Sequence to Pyrazole and Quinoline Derivatives. Molecules, 25(9), Article 2160. https://doi.org/10.3390/molecules25092160

The hydroxy-pyrazole and 3-hydroxy-oxindole motifs have been utilised in several pharma and agrochemical leads but are distinctly underrepresented in the scientific literature due to the limited routes of preparation. We have developed a one-pot proc... Read More about A One-Pot Divergent Sequence to Pyrazole and Quinoline Derivatives.

Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles (2019)
Journal Article
Nicholls, A., Batsanov, A., & Baxendale, I. (2019). Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles. Molecules, 24(22), Article 4154. https://doi.org/10.3390/molecules24224154

A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in... Read More about Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles.

The Synthesis and Utility of Metal-Nitrosophenolato Compounds—Highlighting the Baudisch Reaction (2019)
Journal Article
Nicholls, A., Barber, T., & Baxendale, I. (2019). The Synthesis and Utility of Metal-Nitrosophenolato Compounds—Highlighting the Baudisch Reaction. Molecules, 24(22), https://doi.org/10.3390/molecules24224018

The syntheses of the title compounds demonstrate a privileged introduction of a nitroso (and a hydroxyl via the Baudisch reaction) group to an aromatic ring. These complexes first appeared in the literature as early as 1939, and a range of applicatio... Read More about The Synthesis and Utility of Metal-Nitrosophenolato Compounds—Highlighting the Baudisch Reaction.

A simple and efficient flow preparation of pyocyanin a virulence factor of Pseudomonas aeruginosa (2019)
Journal Article
Mortzfeld, F., Pietruszka, J., & Baxendale, I. (2019). A simple and efficient flow preparation of pyocyanin a virulence factor of Pseudomonas aeruginosa. European Journal of Organic Chemistry, 2019(31-32), 5424-5433. https://doi.org/10.1002/ejoc.201900526

The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product has been facilitated by the use of flow chemistry techniques and immobilised reag... Read More about A simple and efficient flow preparation of pyocyanin a virulence factor of Pseudomonas aeruginosa.

Photochemical Flow Synthesis of 3-Hydroxyazetidines (2019)
Journal Article
Ruggeri, M., Dombrowski, A. W., Djuric, S. W., & Baxendale, I. R. (2019). Photochemical Flow Synthesis of 3-Hydroxyazetidines. ChemPhotoChem, 3(12), 1212-1218. https://doi.org/10.1002/cptc.201900188

A photo-flow Norrish–Yang cyclisation has been devised that delivers 3-hydroxyazetidines in good yields. The high reproducibility and short residence times of the flow process enables easy scaling of the transformation allowing access to these valuab... Read More about Photochemical Flow Synthesis of 3-Hydroxyazetidines.