Novel and convenient to substituted imidazoles

Chang, Yu-An; Chang, Houchen

doi:10.1002/jhet.213

Cited by 4 publications

(1 citation statement)

References 28 publications

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“…The earliest synthetic route for azvudine was reported by Chang . Using ribose as a raw material, the target product azvudine was obtained through 14 steps with a total yield of 2.6%, involving hazardous chlorination, fluorination, and azidation reactions (Scheme B).…”

Section: Introductionmentioning

confidence: 99%

Fully Continuous Flow Synthesis of 2′-Deoxy-2′-fluoro-arabinoside: A Key Intermediate of Azvudine

Chen,

Sun,

et al. 2024

Org. Process Res. Dev.

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Azvudine was approved for the treatment of adult HIV-1 infection in China in 2021, and it was approved for conditional marketing for the treatment of SARS-CoV-2 in China in 2022. In this work, we describe a fully continuous flow synthesis of 2′-deoxy-2′-fluoroarabinoside, a key intermediate for azvudine. The process was accomplished via six chemical transformations, including chlorination, hydrolysis, fluorination, bromination, condensation, and deprotection in six sequential continuous flow devices. Under the optimized process conditions, the total yield was 32.3% with a total residence time of 156 min. Compared with batch conditions, the total yield was doubled, the total reaction time was shortened 16 times, and the E factor was reduced 1.63 times.

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Section: Introductionmentioning

confidence: 99%

Fully Continuous Flow Synthesis of 2′-Deoxy-2′-fluoro-arabinoside: A Key Intermediate of Azvudine

Chen,

Sun,

et al. 2024

Org. Process Res. Dev.

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ChemInform Abstract: Novel and Convenient to Substituted Imidazoles.

Chang

2010

ChemInform

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Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Sacher

Weinreb

2011

Tetrahedron

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A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1.a regioselective Diels-Alder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration.

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Novel and convenient to substituted imidazoles

Abstract: magnified image A one‐pot synthesis of imidazoles has been established from the addition of azides to 2‐amidoacrylates, and this synthetic method demonstrates an efficient synthesis of imidazole‐4‐carboxylates. J. Heterocyclic Chem., (2009).

Cited by 4 publications

References 28 publications

Fully Continuous Flow Synthesis of 2′-Deoxy-2′-fluoro-arabinoside: A Key Intermediate of Azvudine

Fully Continuous Flow Synthesis of 2′-Deoxy-2′-fluoro-arabinoside: A Key Intermediate of Azvudine

ChemInform Abstract: Novel and Convenient to Substituted Imidazoles.

Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

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