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Péter Bana, Róbert Örkényi, Klára Lövei, Ágnes Lakó, G. Túrós, J. Éles, F. Faigl, I. Greiner (2017)
The route from problem to solution in multistep continuous flow synthesis of pharmaceutical compounds.Bioorganic & medicinal chemistry, 25 23
J. Britton, C. Raston (2017)
Multi-step continuous-flow synthesis.Chemical Society reviews, 46 5
Taifur Rahman, T. Wirth (2018)
Safe Use of Hazardous Chemicals in Flow
Bernhard Gutmann, David Cantillo, C. Kappe (2015)
Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients.Angewandte Chemie, 54 23
(2019)
Fürstner A (2019)
S. Peil, A. Fürstner (2019)
Mechanistic Divergence in the Hydrogenative Synthesis of Furans and Butenolides: Ruthenium Carbenes Formed by gem‐Hydrogenation or through Carbophilic Activation of AlkynesAngewandte Chemie (International Ed. in English), 58
Matthew Plutschack, Bartholomäus Pieber, K. Gilmore, P. Seeberger (2017)
The Hitchhiker's Guide to Flow Chemistry ∥.Chemical reviews, 117 18
(2017)
Raston CL (2017)
T. Glasnov (2016)
Continuous-flow chemistry in the research laboratory
A. Stütz, G. Petrányi (1984)
Synthesis and antifungal activity of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphtha lenemethanamine (SF 86-327) and related allylamine derivatives with enhanced oral activity.Journal of medicinal chemistry, 27 12
(1999)
ACH - Models in Chemistry
Sébastien Belot, Adrien Quintard, N. Krause, A. Alexakis* (2010)
Organocatalyzed Conjugate Addition of Carbonyl Compounds to Nitrodienes/Nitroenynes and Synthetic ApplicationsAdvanced Synthesis & Catalysis, 352
Bing Zhou, Qiuyue Wu, Ziyang Dong, Jiaxi Xu, Zhanhui Yang (2019)
Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization.Organic letters, 21 10
M. Baumann, I. Baxendale (2015)
The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistryBeilstein Journal of Organic Chemistry, 11
M. Yamaguchi, Keisuke Shibato, Shingo Fujiwara, I. Hirao (1986)
A Convenient Synthesis of Alkynyl Ketones from EstersSynthesis, 1986
Xiukai Li, Yugen Zhang (2016)
Highly Efficient Process for the Conversion of Glycerol to Acrylic Acid via Gas Phase Catalytic Oxidation of an Allyl Alcohol IntermediateACS Catalysis, 6
N. Neyt, D. Riley (2018)
Batch–flow hybrid synthesis of the antipsychotic clozapineReaction Chemistry and Engineering, 3
N. Ryder (1992)
Terbinafine: Mode of action and properties of the squalene epoxidase inhibitionBritish Journal of Dermatology, 126
F. Bohlmann (1953)
Konstitution und Lichtabsorption, VI. Mitteil.: Zur Deutung von Polyacetylen‐Spektren, sowie Darstellung von Bis‐tert.‐butyl‐decapentain‐(1.3.5.7.9)Chemische Berichte, 86
H Li, D Grassi, L Guénée, T Bürgi, A Alexakis (2014)
10.1002/chem.201390210Chem Eur J, 20
V. Hessel, H. Löwe, F. Schönfeld (2005)
Micromixers—a review on passive and active mixing principlesChemical Engineering Science, 60
T. Allmendinger, C. Angst, H. Karfunkel (1995)
Fluorinated allylic alcohols as building blocksJournal of Fluorine Chemistry, 72
U. Azzena, M. Carraro, L. Pisano, Serena Monticelli, R. Bartolotta, Vittorio Pace (2018)
Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic ChemistryChemsuschem, 12
Vittorio Pace, P. Hoyos, L. Castoldi, P. María, A. Alcántara (2012)
2-Methyltetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry.ChemSusChem, 5 8
D. Aycock (2007)
Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic ReactionsOrganic Process Research & Development, 11
Kiyoshi Watanabe, Noriyuki Yamagiwa, Y. Torisawa (2007)
Cyclopentyl Methyl Ether as a New and Alternative Process SolventOrganic Process Research & Development, 11
Aditya Gupta, Neil Shear (1997)
Terbinafine: an update.Journal of the American Academy of Dermatology, 37 6
Malcolm Darkes, L. Scott, K. Goa (2003)
TerbinafineAmerican Journal of Clinical Dermatology, 4
T. Glasnov (2016)
Continuous-Flow Chemistry in the Research Laboratory: Modern Organic Chemistry in Dedicated Reactors at the Dawn of the 21st CenturyContinuous-Flow Chemistry in the Research Laboratory
Daniel Fitzpatrick, Claudio Battilocchio, S. Ley (2015)
A Novel Internet-Based Reaction Monitoring, Control and Autonomous Self-Optimization Platform for Chemical SynthesisOrganic Process Research & Development, 20
A. Lumbroso, Michael Cooke, B. Breit (2013)
Catalytic asymmetric synthesis of allylic alcohols and derivatives and their applications in organic synthesis.Angewandte Chemie, 52 7
(2018)
Flow Chemistry for the Synthesis of HeterocyclesFlow Chemistry for the Synthesis of Heterocycles
Anne-Catherine Bédard, A. Adamo, Kosi Aroh, M. Russell, Aaron Bedermann, Jeremy Torosian, Brian Yue, K. Jensen, T. Jamison (2018)
Reconfigurable system for automated optimization of diverse chemical reactionsScience, 361
Nelly Tshibalonza, J. Monbaliu (2017)
Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditionsGreen Chemistry, 19
J. Reckamp, Ashira Bindels, Sophie Duffield, Yangmu Liu, E. Bradford, Eric Ricci, Flavien Susanne, Andrew Rutter (2017)
Mixing Performance Evaluation for Commercially Available Micromixers Using Villermaux–Dushman Reaction Scheme with the Interaction by Exchange with the Mean ModelOrganic Process Research & Development, 21
A. Adamo, Rachel Beingessner, M. Behnam, Jie Chen, T. Jamison, K. Jensen, J. Monbaliu, A. Myerson, E. Revalor, David Snead, T. Stelzer, Nopphon Weeranoppanant, S. Wong, Ping Zhang (2016)
On-demand continuous-flow production of pharmaceuticals in a compact, reconfigurable systemScience, 352
Nathan Bowling, Nicola Burrmann, R. Halter, J. Hodges, R. McMahon (2010)
Synthesis of simple diynals, diynones, their hydrazones, and diazo compounds: precursors to a family of dialkynyl carbenes (R(1)-C≡C-C-C≡C-R(2)).The Journal of organic chemistry, 75 19
D. Knight, Heinz Rost, Christopher Sharland, J. Singkhonrat (2007)
A general approach to polysubstituted pyrrolesTetrahedron Letters, 48
J. Balfour, D. Faulds (1992)
Terbinafine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in superficial mycoses.Drugs, 43 2
Erin Skoda, G. Davis, P. Wipf (2012)
Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres.Organic process research & development, 16 1
A three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up.
Journal of Flow Chemistry – Springer Journals
Published: Mar 1, 2022
Keywords: Multistep organometallic reaction; Batch-flow hybrid synthesis; Terbinafine; Enynol
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