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An efficient and scalable synthesis of thiazolo ring fused 2-pyridones using flow chemistry
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0003-1803-2708
Umeå University, Faculty of Science and Technology, Department of Chemistry.
FOI, Swedish Defence Research Agency, CBRN Defence & Security, Umeå, Sweden.
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2021 (English)In: ARKIVOC, ISSN 1551-7004, E-ISSN 1551-7012, Vol. 2020, no 7, p. 365-378Article in journal (Refereed) Published
Abstract [en]

Thiazolino ring fused 2-pyridones are a valuable scaffold with varied and substitution dependent biological activity, accessed primarily by an acyl ketene-imine cycloaddition and rearrangement. Although powerful, some aspects of this chemistry such as the requirement for excess starting material and the production of gas can make larger scale synthesis challenging. Here we describe the development, application and scaling of a continuous flow process allowing larger scale synthesis, with better handling of hazards and more reliable scaling. Optimisation and control of conditions allows for a more efficient synthesis, with a lower equivalence of the acyl ketene precursor required.

Place, publisher, year, edition, pages
Arkat , 2021. Vol. 2020, no 7, p. 365-378
Keywords [en]
Acyl ketene, Design of experiments, Flow chemistry, Heterocycle, Pyridone, Thiazolo
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-181828DOI: 10.24820/ARK.5550190.P011.445ISI: 000746840700002Scopus ID: 2-s2.0-85102694748OAI: oai:DiVA.org:umu-181828DiVA, id: diva2:1542145
Available from: 2021-04-06 Created: 2021-04-06 Last updated: 2023-09-05Bibliographically approved

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Cairns, Andrew G.Sarkar, SouvikSingh, PardeepAlmqvist, Fredrik

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Citation style
  • apa
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