Synthesis of new heterocyclic resveratrol analogues in milli- and microreactors: intensification of the Wittig reaction

IF 2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Flow Chemistry Pub Date : 2022-08-05 DOI:10.1007/s41981-022-00239-9

Milena Mlakić, Lucija Rajič, Anabela Ljubić, Vitomir Vušak, Bruno Zelić, Martin Gojun, Ilijana Odak, Ivona Čule, Ivana Šagud, Anita Šalić, Irena Škorić

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引用次数: 5

Abstract

Resveratrol is a natural bioactive non-flavonoid polyphenol that protects from cardiovascular disease, neurodegenerative diseases and various cancers. Unfortunately, the amounts of resveratrol in plants are low and therefore, chemical synthesis is still the main way to obtain this valuable structure. In this work, Wittig reaction was chosen as the synthetic route for the study on technology influence in batch vs. micro- or milliflow reactors during the production of new resveratrol-like compounds. A series of reactions was carried out by batch synthesis, and intensified in a milli- and a microreactor, changing the reaction conditions to increase the efficiency and productivity of the process. Results were compared based on conversion, yield, productivity and trans/cis ratio. Similar yields and conversions were obtained in all reaction systems, but in much shorter time in the milli- and microscale compared to the batch reactor. On the other hand, higher productivities were obtained in the millireactor and microreactor, making them better systems for the proposed reactions of new heterocyclic resveratrol analogues synthesis.

Graphical abstract

Abstract Image

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在微反应器和微反应器中合成新的杂环白藜芦醇类似物:强化Wittig反应

白藜芦醇是一种天然的生物活性非类黄酮多酚，可预防心血管疾病、神经退行性疾病和各种癌症。不幸的是，植物中白藜芦醇的含量很低，因此，化学合成仍然是获得这种有价值结构的主要方法。本文选择Wittig反应作为合成路线，研究了间歇反应器与微、毫流反应器生产新型白藜芦醇类化合物的工艺影响。通过间歇式合成进行了一系列反应，并在微反应器和微反应器中进行了强化，改变了反应条件，提高了反应的效率和生产率。结果根据转化率、产量、生产率和反顺比进行比较。在所有的反应系统中都获得了相似的产率和转化率，但在毫微米尺度上与间歇式反应器相比所需的时间要短得多。另一方面，微反应器和微反应器的反应效率较高，是合成新型杂环白藜芦醇类似物的较好系统。图形抽象

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来源期刊

Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

6.40

自引率

3.70%

发文量

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.