用于合成有机叠氮化物和 1,2,3-三唑的壬烯呋喃叠氮化物 (NfN3) 的连续制备和反应

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Flow Chemistry Pub Date : 2024-07-04 DOI:10.1007/s41981-024-00327-y
Sebastian P. Green, Hannah C. Broderick, Katherine M. P. Wheelhouse, Jason P. Hallett, Philip W. Miller, James A. Bull
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引用次数: 0

摘要

有机叠氮化物广泛用于有机合成。连续流工艺可用于绕过它们的分离,因此可有效减轻这些潜在有毒和易爆试剂带来的危害。据报道,壬酰基叠氮化物是一种有效、稳定、相对安全的重氮转移试剂,可用于从胺中制备叠氮化物,从而避免使用烷基卤化物。在此,我们展示了连续流合成和纯化壬烯丙基叠氮化物的过程,并通过膜过滤分离出纯净的试剂。纯试剂用于从伯胺制备有机叠氮化物,然后用于合成三唑类化合物。在半批次平行阵列中,通过 CuAAC 点击反应从伯胺和炔烃制备了多种三唑类化合物,包括抗癫痫药物鲁非那胺(Rufinamide),而无需分离烷基叠氮化物中间体。此外,还设计并演示了一种伸缩式两级连续流工艺,可通过相同的 CuAAC 反应生成三唑,从而避免了对中间反应叠氮化物的处理。
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Continuous preparation and reaction of nonaflyl azide (NfN3) for the synthesis of organic azides and 1,2,3-triazoles

Organic azides are widely used in organic synthesis. Continuous flow processing can be used to bypass their isolation, and can therefore be useful in mitigating the hazards associated with these potentially toxic and explosive reagents. Nonaflyl azide has been reported as an effective, bench-stable, and relatively safe diazo transfer reagent that can be useful in the preparation of azides from amines and so avoid the use of alkyl halides. Here we demonstrate the synthesis and purification of nonaflyl azide in continuous flow with isolation of the neat, pure reagent by membrane filtration. The neat reagent was used in the preparation of organic azides from primary amines, and then applied to the synthesis of triazoles. A variety of triazoles, including the antiseizure drug Rufinamide, were prepared from primary amines and alkynes via the CuAAC click reaction in a semi-batch parallel array without isolation of alkyl azide intermediates. A telescoped two-stage continuous flow process was also designed and demonstrated to form triazoles via the same CuAAC reaction, which avoids the handling of the intermediate reactive azides.

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来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
期刊最新文献
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