Rapid and High‐Yield Electrosynthesis of Benzisoxazole and Some Derivatives,ChemElectroChem

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Rapid and High‐Yield Electrosynthesis of Benzisoxazole and Some Derivatives
ChemElectroChem ( IF 3.5 ) Pub Date : 2018-11-30 , DOI: 10.1002/celc.201801321
Seyyedamirhossein Hosseini ₁ , Seth A. Bawel ₁ , Mohammad S. Mubarak ₂ , Dennis G. Peters ₁

Affiliation

Cyclic voltammetry and controlled‐potential (bulk) electrolysis have been used to explore the electrochemical reduction of o‐nitrobenzaldehyde (o‐NBA) and 8 other aldehydes and ketones at glassy carbon cathodes in dimethylformamide containing various tetraalkylammonium tetrafluoroborate salts along with a proton donor (4‐chlorophenol). Cyclic voltammograms for reduction of o‐NBA exhibit three cathodic peaks attributable in succession to (a) one‐electron generation of the nitro radical‐anion, (b) three‐electron formation of the hydroxylamine, and (c) two‐electron production of benzisoxazole (anthranil). These findings have been employed to develop efficient controlled‐potential (bulk) electrosyntheses of the following compounds: benzisoxazole, methylbenzo[c]isoxazole, [1,3]dioxolo[4′,5′,4,5]benzo[1,2‐c]isoxazole, naphtho[2,3‐c]isoxazole, 6‐chlorobenzo[c]isoxazole, 6‐methoxybenzo[c]isoxazole, 3‐methyl‐benzo[c]isoxazole, 3‐isopropylbenzo[c]isoxazole, and 3‐phenylbenzo[c]isoxazole. In addition, we have examined the use of a variety of proton donors to optimize the production of the desired product, and we have been able to recover the proton donor at the conclusion of the electrosynthesis. In each case, the synthesized product was separated by means of normal phase chromatography and identified with the aid of NMR spectros‐copy, gas chromatography (GC), and gas chromatography‐mass spectrometry (GC‐MS). Isolated yields of the desired products range from 63 to 92 %. Moreover, our electrosyntheses are catalyst‐free, environmentally green, and rapid (∼30 min).

中文翻译：

苯并异恶唑及其衍生物的快速高产电合成

循环伏安法和控制电位（本体）电解已用于探索邻硝基苯甲醛（o NBA）和其他8种醛和酮在含有各种四烷基硼酸四烷基铵盐和质子供体的二甲基甲酰胺中的玻璃碳阴极上的电化学还原（ 4-氯苯酚）。减少o的循环伏安图‐NBA表现出三个阴极峰，可归因于（a）硝基自由基阴离子的单电子生成，（b）羟胺的三电子形成，以及（c）苯并异恶唑（蒽基）的双电子生成。这些发现已被用于开发以下化合物的有效电势控制（本体）：苯并异恶唑，甲基苯并[c]异恶唑，[1,3]二恶唑[4'，5'，4,5]苯并[1,2] -c]异恶唑，萘[2,3-c]异恶唑，6-氯苯并[c]异恶唑，6-甲氧基苯并[c]异恶唑，3-甲基-苯并[c]异恶唑，3-异丙基苯并[c]异恶唑和3-苯基苯并[c]异恶唑。另外，我们已经研究了使用各种质子供体来优化所需产物的生产，并且我们已经能够在电合成结束时回收质子供体。在每种情况下，通过正相色谱法分离合成的产物，并借助NMR光谱，气相色谱（GC）和气相色谱-质谱（GC-MS）进行鉴定。所需产物的分离产率为63-92％。此外，我们的电合成不含催化剂，绿色环保且反应迅速（约30分钟）。

更新日期：2018-11-30

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