ArticleAngewandte Chemie (International ed. in English)2017
A Unified Continuous Flow Assembly-Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 160 citations in OpenAlex.
- Ultrafast Laser-Enabled 3D Glass Microchannel Reactors.Sensors (Basel, Switzerland) · 2025Review
- The Role of Flow Chemistry on the Synthesis of Pyrazoles, Pyrazolines and Pyrazole-Fused Scaffolds.Molecules (Basel, Switzerland) · 2025Review
- Progress in Continuous Flow Synthesis of Hydrogen-Bonded Organic Framework Material Synthons.Molecules (Basel, Switzerland) · 2024Review
- Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps.Beilstein journal of organic chemistry · 2024Review
- Photocatalytic Boryl Radicals Triggered Sequential B─N/C─N Bond Formation to Assemble Boron-Handled Pyrazoles.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethylBeilstein journal of organic chemistry · 2024Article
- One-Pot (3 + 2) Cycloaddition-Isomerization-Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives.The Journal of organic chemistry · 2023Article
- Bayesian Self-Optimization for Telescoped Continuous Flow Synthesis.Angewandte Chemie (International ed. in English) · 2023Article
- Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions.Organic letters · 2022Article
- Understanding flow chemistry for the production of active pharmaceutical ingredients.iScience · 2022Review
- A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries.Beilstein journal of organic chemistry · 2021Review
- Development and Scale-up of the Rapid Synthesis of Triphenyl Phosphites in Continuous Flow.ACS omega · 2020Article
- Automated radial synthesis of organic molecules.Nature · 2020Article
- Continuous-flow synthesis of 3,5-disubstituted pyrazolesRSC advances · 2019Article
- Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.Nature communications · 2019Article
- 7-Step Flow Synthesis of the HIV Integrase Inhibitor Dolutegravir.Angewandte Chemie (International ed. in English) · 2018Article
- The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.Angewandte Chemie (International ed. in English) · 2018Review
- The assembly and use of continuous flow systems for chemical synthesis.Nature protocols · 2017Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.