Applications of Knoevenagel condensation reaction in the total synthesis of natural products

Heravi, Majid M.; Janati, Fatemeh; Zadsirjan, Vahideh

doi:10.1007/s00706-020-02586-6

Cited by 62 publications

(21 citation statements)

References 304 publications

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“…Molecules synthesized by the Knoevenagel reaction directly used in products are also widespread. These entail a broad range of products used for an enormous quantity of purposes, among which: pesticides, antifungal products, anti-bacterial products, but also specific compounds for the use of enzyme regulation (15)(16)(17). In medicinal chemistry, Knoevenagel products show pharmacological actions such as antiviral, antitubercular, anti-Parkinson's, anti-diabetic, anti-oxidant, and anti-cancer activity.…”

Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

113

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The formation of carbon-carbon bonds is a quest that has required a lot of research throughout the last 125 years of history of chemistry. The creation of these bonds is key to producing a wide variety of advanced products with great societal importance. In the past, the Knoevenagel reaction entailed a big part of these reactions. All the Knoevenagel reactions are performed with nitrogen-based catalysts, categorized as tertiary amines, secondary amines, primary amines, and ammonium salts. These catalysts operate through different reaction paths, with very deviant intermediates concerning each category. Subsequently, these intermediates create new research opportunities considering their catalytic activity. Some remarks are made in the context of green chemistry, with quantitative analysis using e-factor calculations. In this perspective, the importance of Knoevenagel chemistry exemplified, which is repeatedly overlooked throughout history.

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Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

113

View full text Add to dashboard Cite

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“…Among these, Knoevenagel condensation is known to play a pivotal role in the total synthesis of organic compounds (Heravi et al. 2020), including sterols (List 2010; Woodward et al. 1952).…”

Section: Discussionmentioning

confidence: 99%

“…Many reactions have been reported to be facilitated by the free amino groups at the C2 position: a variety of C-C bond forming reactions including aldol reactions, Knoevenagel condensation, nitroaldol reaction, Michael reaction (K€ uhbeck et al 2012), and the synthesis of a-amino nitriles and imines (Dekamin et al 2013). Among these, Knoevenagel condensation is known to play a pivotal role in the total synthesis of organic compounds (Heravi et al 2020), including sterols (List 2010;Woodward et al 1952). Since chitinous plates in C. ovoidea are sometimes located along the vacuole membrane or even form a part of the vacuole membrane (Fig.…”

Section: Reactive Site For Metabolic Functionsmentioning

confidence: 99%

Abundant Chitinous Structures in Chilostomella (Foraminifera, Rhizaria) and Their Potential Functions

Nomaki

Chen

Oda

et al. 2020

J Eukaryotic Microbiology

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Benthic foraminifera, members of Rhizaria, inhabit a broad range of marine environments and are particularly common in hypoxic sediments. The biology of benthic foraminifera is key to understanding benthic ecosystems and relevant biogeochemical cycles, especially in hypoxic environments. Chilostomella is a foraminiferal genus commonly found in hypoxic deep-sea sediments and has poorly understood ecological characteristics. For example, the carbon isotopic compositions of their lipids are substantially different from other co-occurring genera, probably reflecting unique features of its metabolism. Here, we investigated the cytoplasmic and ultrastructural features of Chilostomella ovoidea from bathyal sediments of Sagami Bay, Japan, based on serial semithin sections examined using an optical microscope followed by a three-dimensional reconstruction, combined with TEM observations of ultra-thin sections. Observations by TEM revealed the presence of abundant electron-dense structures dividing the cytoplasm. Based on histochemical staining, these structures are shown to be composed of chitin. Our 3D reconstruction revealed chitinous structures in the final seven chambers. These exhibited a plate-like morphology in the final chambers but became rolled up in earlier chambers (toward the proloculus). These chitinous, plate-like structures may function to partition the cytoplasm in a chamber to increase the surface/volume ratio and/or act as a reactive site for some metabolic functions.

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“…Knoevenagel condensation, a reaction named after being established by the German chemist Emil Knoevenagel [ 25 , 26 , 27 ], is commonly used in organic synthesis and is of particular utility in total synthesis [ 28 ]. In our case, we applied this type of reaction to obtain chromone derivatives, in particular ( E )-3-styryl-4 H -chromen-4-ones 10 [ 29 ].…”

Section: Microwave-assisted Knoevenagel Condensation In 3-styryl-4 H -Chromen-4-ones Synthesismentioning

confidence: 99%

Microwave Irradiation: Alternative Heating Process for the Synthesis of Biologically Applicable Chromones, Quinolones, and Their Precursors

2021

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Microwave irradiation has become a popular heating technique in organic synthesis, mainly due to its short reaction times, solventless reactions, and, sometimes, higher yields. Additionally, microwave irradiation lowers energy consumption and, consequently, is ideal for optimization processes. Moreover, there is evidence that microwave irradiation can improve the regioselectivity and stereoselectivity aspects of vital importance in synthesizing bioactive compounds. These crucial features of microwave irradiation contribute to its inclusion in green chemistry procedures. Since 2003, the use of microwave-assisted organic synthesis has become common in our laboratory, making our group one of the first Portuguese research groups to implement this heating source in organic synthesis. Our achievements in the transformation of heterocyclic compounds, such as (E/Z)-3-styryl-4H-chromen-4-ones, (E)-3-(2-hydroxyphenyl)-4-styryl-1H-pyrazole, (E)-2-(4-arylbut-1-en-3-yn-1-yl)-4H-chromen-4-ones, or (E)-2-[2-(5-aryl-2-methyl-2H-1,2,3-triazol-4-yl)vinyl]-4H-chromen-4-ones, will be discussed in this review, highlighting the benefits of microwave irradiation use in organic synthesis.

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Applications of Knoevenagel condensation reaction in the total synthesis of natural products

Cited by 62 publications

References 304 publications

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Abundant Chitinous Structures in Chilostomella (Foraminifera, Rhizaria) and Their Potential Functions

Microwave Irradiation: Alternative Heating Process for the Synthesis of Biologically Applicable Chromones, Quinolones, and Their Precursors

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