Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

• Cinnamic acid derivatives represent a significant class of biologically active compounds exhibiting a broad spectrum of activities, such as antifungal, antidengue, antimetastatic, antimicrobial, antibacterial, and anticancer properties. Their preparation has attracted considerable attention due to their

• the past five years is presented, particularly emphasizing the active scaffolds of bioactive cinnamic acid derivatives. The review provides a strategic overview of alternative synthetic routes and highlights the latest innovations, including more efficient, highly selective, and environmentally

• examining these methodologies, the paper underscores their role in expanding the utility of cinnamic acid derivatives and addressing prevailing challenges. Keywords: biologically active; cinnamic acid derivatives; environmentally sustainable; synthetic methodologies; Review 1 Introduction Cinnamic acid is

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• colleagues reported on the photocatalytic decarboxylative alkenylation reactions facilitated by cooperative NaI/PPh3 catalysis [9]. These conversions involved the coupling of 1,1-diarylethene/cinnamic acid derivatives (1, 2) with redox-active esters 3 (Scheme 3). Notably, the reactions were driven by blue

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• cyclohexyl-based chiral auxiliaries [93]. While studying the effect of chiral auxiliaries on the enantioselective electroreduction of cinnamic acid derivatives, which resulted in the corresponding hydrodimers, Kise and his group investigated a number of chiral auxiliaries and found that chiral auxiliary

• transformations, Feroci and Inesi developed a stereoselective carboxylation of cinnamic acid derivatives 171 substituted with chiral auxiliaries [99]. The substrate 171 was subjected to galvanostatic reduction under CO2 atmosphere in an undivided cell. Carboxylation followed by treatment with diazomethane

• alkylation, reduction and catalytic hydrogenolysis, (+)-199 was converted to desired product (−)-200 with 80% ee (Scheme 62). An electrochemical method for the asymmetric oxidative dimerization of cinnamic acid derivatives was developed by Watanabe in 2016 [109]. The substrates for the electrochemical

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• products. Recently, Jacobsen and co-workers reported a highly enantioselective gem-difluorination of various cinnamic acid derivatives through the same oxidative rearrangement (Scheme 16) [68]. During the catalysts screening, they found that the benzylic unit in the catalysts was essential for a high

• aminofluorination of alkenes [62]. Catalytic difluorination of alkenes with Selectfluor [63]. Iodoarene-catalyzed 1,2-difluorination of alkenes [64]. Iodoarene-catalyzed asymmetric fluorination of styrenes [64][65]. Gem-difluorination of styrenes [67]. Asymmetric gem-difluorination of cinnamic acid derivatives [68

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki–Heck cross-coupling reaction

• Jerzy Zakrzewski and
• Bogumiła Huras

Beilstein J. Org. Chem. 2015, 11, 1155–1162, doi:10.3762/bjoc.11.130

• Jerzy Zakrzewski Bogumila Huras Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland 10.3762/bjoc.11.130 Abstract Cinnamic acid derivatives bearing a nitroxyl moiety (2,2,6,6-tetramethyl-1-oxyl-4-piperidyl 3-E-aryl acrylates) were synthesized in 30–100% yield using a

• -oxyl; cinnamates; Mizoroki–Heck cross-coupling reaction; nitroxides; Introduction Cinnamic acid derivatives are known as biologically active compounds. Cinnamic acid and its hydroxy derivatives bearing a phenolic moiety such as coumaric, caffeic, ferulic, sinapinic, and chlorogenic acids [2][3][4][5

• ][6], simple cinnamic acid derivatives (esters, amides, etc.), and prenylated cinnamates [4], have been proved to be effective as antioxidants [2][7], radical scavengers [2], antimicrobials [2][7][8], antibacterials [2], antivirals [2][7], and fungicides [2][7][8]. Cinnamic derivatives have also been

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

• Taiki Kojima,
• Rika Obata,
• Tsuyoshi Saito,
• Yasuaki Einaga and
• Shigeru Nishiyama

Beilstein J. Org. Chem. 2015, 11, 200–203, doi:10.3762/bjoc.11.21

• . As shown in Figure 1, the radical intermediate derived from phenylacrylate through a one-electron reduction (right) differs from that obtained by anodic oxidation of 4-hydroxyphenyl-1-propene (left). Therefore, the reductive dimerization of cinnamic acid derivatives was expected to provide access to

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

• Jincan Zhao,
• Hong Fang,
• Jianlin Han and
• Yi Pan

Beilstein J. Org. Chem. 2013, 9, 1718–1723, doi:10.3762/bjoc.9.197

• cinnamic acid derivatives under the optimized conditions (Table 1, entry 8). As shown in Scheme 1, almost all of the tested substrates worked well in this reaction. Several substituents on the aromatic ring were tolerated and the position of these substituents showed almost no effect on the chemical yield

Hydroxyapatite supported caesium carbonate as a new recyclable solid base catalyst for the Knoevenagel condensation in water

• Monika Gupta,
• Rajive Gupta and
• Medha Anand

Beilstein J. Org. Chem. 2009, 5, No. 68, doi:10.3762/bjoc.5.68

• antimetabolites [19] and in particular as synthetic intermediates for many heterocyclic compounds [20]. Moreover, cinnamic acid derivatives have major applications in many fields and find applications as plasticizers, perfumes, aroma compounds [21], lubricants, etc. The diverse range of catalysts known to effect