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A Unified Continuous Flow Assembly‐Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines

Britton, Joshua ; Jamison, Timothy F.

Angewandte Chemie (International ed.), 2017-07, Vol.56 (30), p.8823-8827 [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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Título:
A Unified Continuous Flow Assembly‐Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines
Autor: Britton, Joshua ; Jamison, Timothy F.
Assuntos: active pharmaceutical ingredients ; Agrochemicals ; Alkylation ; Alkynes ; Amines ; Aromatic compounds ; Assembly ; assembly line synthesis ; Azoles ; Catalysts ; Chemical synthesis ; Coiling ; Coils ; Communication ; Continuous flow ; Cores ; Cycloaddition ; Drugs ; Fluorination ; Heterocyclic compounds ; Measles ; Modules ; multi-step continuous flow synthesis ; Pyrazole ; Pyrazoles ; Reactor cores ; Reactors
É parte de: Angewandte Chemie (International ed.), 2017-07, Vol.56 (30), p.8823-8827
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Supporting information for this article is given via a link at the end of the document.
Descrição: A rapid and modular continuous flow synthesis of highly functionalized fluorinated pyrazoles and pyrazolines has been developed. Flowing fluorinated amines through sequential reactor coils mediates diazoalkane formation and [3+2] cycloaddition to generate more than 30 azoles in a telescoped fashion. Pyrazole cores are then sequentially modified through additional reactor modules performing N‐alkylation and arylation, deprotection, and amidation to install broad molecular diversity in short order. Continuous flow synthesis enables the safe handling of diazoalkanes at elevated temperatures, and the use of aryl alkyne dipolarphiles under catalyst‐free conditions. This assembly‐line synthesis provides a flexible approach for the synthesis of agrochemicals and pharmaceuticals, as demonstrated by a four‐step, telescoped synthesis of measles therapeutic, AS‐136A, in a total residence time of 31.7 min (1.76 g h−1). Reaction modularity meets flow: Assembly lines have been used to synthesize highly functionalized pyrazoles and pyrazolines on route to agrochemicals and pharmaceuticals through multi‐step, continuous flow synthesis.
Editor: Germany: Wiley Subscription Services, Inc
Idioma: Inglês

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A Unified Continuous Flow Assembly‐Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines

Britton, Joshua ; Jamison, Timothy F.

Germany: Wiley Subscription Services, Inc

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