Baxendale GroupAdvanced synthetic chemistry, engineered for scaleDepartment of Chemistry

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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 ACS Pharmacol. Transl. Sci.
Graphical abstract for Discovery of a potent dual inhibitor of aromatase and aldosterone synthase

Journal article

Discovery of a potent dual inhibitor of aromatase and aldosterone synthase

Tinivella, A.; Banchi, M.; Gambacorta, G.; Borghi, F.; Orlandi, P.; Baxendale, I. R; Di Paolo, A.; Bocci, G.; Pinzi, L.; Rastelli, G.

ACS Pharmacol. Transl. Sci. · 2023 · 6 · 1870–1883

Synthetic and heterocyclic chemistry

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 major cause…

Open DOIPDF
Cover of Data in Brief
Graphical abstract for Spectroscopic dataset of Hedione’s derivatives gathered during process development

Journal article

Spectroscopic dataset of Hedione’s derivatives gathered during process development

Sharley, J. S.; Gambacorta, G.; Pérez, A. M. C.; Ferri, E. E.; Miranda, A. F.; Quesada, J. S.; Baxendale, I. R.

Data in Brief · 2023 · 46 · 108801(1)–108801(24)

Synthetic and heterocyclic chemistryRoute design and process chemistry

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 September 2021…

Open DOIPDF
Cover of Molbank
Graphical abstract for 6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride

Journal article

6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride

Nicholls, A. J.; Baxendale, I. R.

Molbank · 2022 · 2022 · M1339-1–M1339-8

Synthetic and heterocyclic chemistry

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 medicinal and …

Open DOIPDF
Cover of Tetrahedron
Graphical abstract for A Simple One-Pot Oxidation Protocol for the Synthesis of Dehydrohedione from Hedione

Journal article

A Simple One-Pot Oxidation Protocol for the Synthesis of Dehydrohedione from Hedione

Sharley, J. S.; Gambacorta, G.; Collado Pérezb, A. M.; Ferri, E. E.; Miranda, A. F.; Fernández, I. F.; Quesada, J. S.; Baxendale, I. R.

Tetrahedron · 2022 · 126 · 133068(1)–133068(11)

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineering

A new method of oxidising Hedione 1 to dehydrohedione 2, a highly valuable target in the flavour and fragrance industry, was developed based on α-chlorination-elimination. The spontaneous elimination of the α-chloro intermediate 5 in methanol was unprecedente…

Open DOIPDF
Cover of Org. Process Res. Dev.
Graphical abstract for Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone

Journal article

Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone

Gambacorta, G.; Baxendale, I. R.

Org. Process Res. Dev. · 2022 · 26 · 422–430

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineering

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 accumulation …

Open DOIPDF
Cover of Euro. J. Med. Chem.
Graphical abstract for Development of α,7α-Dihydroxy-6α-ethyl-24-nor-5b-Cholan-23-Sulfate Sodium Salt (INT-767): Process Optimization, Synthesis and Characterization of Metabolites

Journal article

Development of α,7α-Dihydroxy-6α-ethyl-24-nor-5b-Cholan-23-Sulfate Sodium Salt (INT-767): Process Optimization, Synthesis and Characterization of Metabolites

Cerra, B.; Venturoni, F.; Souma, M.; Ceccarelli, G.; Lozza, A. M.; Passeri, D.; De Franco, F.; Baxendale, I. R.; Pellicciari, R.; Macchiarulo, A.; Gioiello, A.

Euro. J. Med. Chem. · 2022 · 242 · 114652(1)–114652(15)

Synthetic and heterocyclic chemistryRoute design and process chemistry

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 major cause…

Open DOIPDF
Cover of Tetrahedron
Graphical abstract for Further Investigations into Imine-Mediated Formation of Allylic Nitro Compounds

Journal article

Further Investigations into Imine-Mediated Formation of Allylic Nitro Compounds

Sharley, J. S.; Gambacorta, G.; Collado Pérez, A. M.; Ferri, E. E.; Miranda, A. F.; Quesada, J. S.; Baxendale, I. R.

Tetrahedron · 2022 · 126 · 133058(1)–133058(14)

Synthetic and heterocyclic chemistryRoute design and process chemistry

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 construc…

Open DOIPDF
Cover of F1000Research
Graphical abstract for Identification of potential biological targets of oxindole scaffolds via in silico repositioning strategies

Journal article

Identification of potential biological targets of oxindole scaffolds via in silico repositioning strategies

Tinivella, A.; Pinzi, L.; Gambacorta, G.; Baxendale, I. R. Rastelli, G.

F1000Research · 2022 · 22 · 1–16

Synthetic and heterocyclic chemistry

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 reduced attrition rat…

Open DOIPDF
Cover of Molbank
Graphical abstract for 4,4’-(Pyridin-4-ylmethylene)dibenzonitrile

Journal article

4,4’-(Pyridin-4-ylmethylene)dibenzonitrile

Lancaster, B. M. J.; Nicholls, A. J.; Baxendale, I. R.

Molbank · 2021 · 2021 · M1302-1–M1302-5

Synthetic and heterocyclic chemistry

methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual SNAr process, to form a novel triarylmethane structure. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis…

Open DOIPDF
Cover of Beilstein J. Org. Chem.
Graphical abstract for A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Journal article

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta, G.; Sharley, J. S.; Baxendale, I. R.

Beilstein J. Org. Chem. · 2021 · 17 · 1181–1312

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

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 highlights the p…

Open DOIPDF
Cover of Reactions
Graphical abstract for Benzo[1,2,3]dithiazole Compounds: A History of Synthesis and Their Renewed Applicability in Materials and Synthetic Chemistry, Originating from the Herz Reaction

Journal article

Benzo[1,2,3]dithiazole Compounds: A History of Synthesis and Their Renewed Applicability in Materials and Synthetic Chemistry, Originating from the Herz Reaction

A. J. Nicholls; I. R. Baxendale

Reactions · 2021 · 2 · 175–208

Synthetic and heterocyclic chemistryRoute design and process chemistry

The benzo[1,2,3]dithiazole is a unique heteroaromatic functionality whose conjugated profile instils some fascinating electronic properties. This has been historically recognized in the design and manufacture of organic dyes early last century. Although, with…

Open DOIPDF
Cover of J. Org. Chem.
Graphical abstract for Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

Journal article

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

Murie, V. E.; Nicolino, P. V.; dos Santos, T.; Gambacorta, G.; R. H. V. Nishimura, R. H. V., Perovani, I. S.; Furtado, L. C.; Costa-Lotufo, L. V.; de Oliveira, A. M.; Vessecchi, R.; Baxendale, I. R.; Clososki, G. C.

J. Org. Chem. · 2021 · 86 · 13402–13419

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineering

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 intermediat…

Open DOIPDF