One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

• Gui-Feng Kang and
• Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

• discovery as versatile tools for the construction of different biologically active compounds by combining three or more starting materials into a single product in one convergent chemical step [19][20][21][22][23]. Among multicomponent reactions, aldehydes have emerged as one of the most useful class of

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration–oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles

• Lívia Dikošová,
• Júlia Laceková,
• Ondrej Záborský and
• Róbert Fischer

Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112

• of N/O-containing heterocycles used as the key intermediates in the synthesis of more complex cyclic and acyclic compounds, including various biologically active molecules. Here, we present a fast and highly stereoselective approach towards both C-3/4-cis and C-3/4-trans isomers of 3-substituted

• ) represent a very important class of N/O-containing heterocycles used as the key intermediates in the synthesis of more complex cyclic and acyclic compounds, including various biologically active molecules [1][2][3][4][5][6]. In this regard, we have recently developed new methods for the preparation of 4,5

Anthelmintic drug discovery: target identification, screening methods and the role of open science

• Frederick A. Partridge,
• Ruth Forman,
• Carole J. R. Bataille,
• Graham M. Wynne,
• Marina Nick,
• Angela J. Russell,
• Kathryn J. Else and
• David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

• derivative has been the basis of schistosomiasis treatment for over 30 years [20]. PZQ is currently administered as a racemic mixture (Figure 1), despite the (R)-enantiomer being the biologically active form [41]. As will be discussed later in this review, there has been success in producing the active

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

• Dragana Vuk,
• Irena Škorić,
• Valentina Milašinović,
• Krešimir Molčanov and
• Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

• numerous biologically active natural compounds (Figure 1) [4][5][6][7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical

• structure the prepared compounds 1–12 are candidates for biological assays. The novel styryl derivatives 3–7 and 12 could also find application in further research for functionalization of the bicyclo[3.2.1.]octadiene core. Known biologically active bicyclo[3.2.1]octenes/octadienes. Previously prepared

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

• Valeria Nori,
• Antonio Arcadi,
• Armando Carlone,
• Fabio Marinelli and
• Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

• aminopalladation/reductive elimination. Keywords: alkynylanilines; arylboronic acids; indoles; isoquinolinones; palladium; Introduction The isoquinolinone nucleus is a key constituent of many natural products [1][2][3] and pharmaceuticals [4][5][6]. Substituted isoquinolinones have been found in biologically

• active small molecules that exhibit antihypertensive activity [7][8]. Moreover, these heterocycles can be used as 5-HT3 antagonists [9], rho kinase inhibitors [10], thymidylate synthetase inhibitors [11], PARP-1 inhibitors [12], melatonin MT1 and MT2 receptor agonist [13], and fascin-targeted

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

• Mio Matsumura,
• Tsutomu Takahashi,
• Hikari Yamauchi,
• Shunsuke Sakuma,
• Yukako Hayashi,
• Tadashi Hyodo,
• Tohru Obata,
• Kentaro Yamaguchi,
• Yasuyuki Fujiwara and
• Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

• University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan 10.3762/bjoc.16.94 Abstract Most heteroaryl selenides and diselenides are biologically active, with

• of UVA-induced stress [17], and bis(2-alkylindol-3-yl) selenides III exhibit antitumor activity toward HT-1080 and MG-22A tumor cell lines [18]. The imidazo[1,2-a]pyridine ring is also an important aromatic heterocycle because its derivatives are biologically active and play an important role in

• mechanisms are currently underway in our group. Biologically active selenides and diselenides having heteroaryl groups. Ortep drawings of 2a (a and b) and 3a (c and d, thermal elipsoids indicate 50% probability). The synthesis of bis(2-arylimidazopyridin-3-yl) diselenides. Reaction conditions: 1 (2 mmol), Se

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

• Yongsu Li,
• Bendu Pan,
• Xuefeng He,
• Wang Xia,
• Yaqi Zhang,
• Hao Liang,
• Chitreddy V. Subba Reddy,
• Rihui Cao and
• Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

• from chemists because of their widespread appearance in biologically active compounds [1][2][3][4] such as vancomycin [5] and korupensamine A [6] and as useful chiral ligands in asymmetric catalysis. Different strategies with various metals and phosphine ligands had been successfully employed for the

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• biologically active compounds [104]. These compounds can be trapped with nucleophiles to produce the α-amino-substituted compounds, and be employed as substrates for a variety of chemical transformations such as Ugi- and Mannich-type reactions. In this regard, Seeberger and co-workers reported the primary

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• biologically validated scaffolds [8][9][10], referred to as privileged structures in medicinal chemistry [11][12][13][14]. Spanning unexplored chemical space, DOS strategies have been successfully applied to the generation of biologically active libraries for screening, leading to the discovery of medicinally

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

• Péter Bagi,
• Réka Herbay,
• Nikolett Péczka,
• Zoltán Mucsi,
• István Timári and
• György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

• -coupled transformations [18][22][23]. Polycyclic compounds incorporating a P-heterocyclic moiety are of special importance due to their optoelectronic properties and applications [24][25][26]. Moreover, a few biologically active 5-membered P-heterocyclic derivatives are also known, which showed promising

• importance for biologically active compounds, as specific functional groups are necessary to have a desired biological activity. Considering the functionalization of the five-membered P-heterocycles, the derivatives containing double bond(s) (i.e., phospholenes or phospholes) are of special importance, as a

• × 3.0 mL dichloromethane. The organic phase dried (Na2SO4), evaporated to give 0.15 g (81%) of 1-phenyl-3-methyl-2-phospholene oxide (4a). The results are summarized in Table 2 and Scheme 1. Examples for catalytically or biologically active molecules containing five-membered P-heterocyclic rings

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• agent [12]. Piperazinyl amide fragments have the ability to form several hydrogen bonds, modulate the acid–base equilibrium constant and change the octanol–water partition coefficient [13]. They are considered as the basic motif for designing many biologically active molecules [14][15]. Some piperazinyl

• %) without the formation of byproducts [21]. Given the flexible 18β-glycyrrhetinic acid scaffold in the design of biologically active compounds, a novel and efficient method was reported to prepare C3 ester derivatives or/and C30 piperazinyl amides (c). 18β-Glycyrrhetinic acid belongs to the class of ursane

• biologically active substances. According to the first method, compound 12 reacted with morpholine in the presence of K2CO3/I2 to give compound 13, followed by successive amidation and N-Boc deprotection gave compound 17. It is noteworthy that the carboxyl group of compound 12 did not react with inorganic

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• the catalytic system and large-scale synthesis of products, which would further transform into biologically active indole-derived compounds, are further advantages of this protocol. Structures of trifluoromethylated compounds and their biological activities. Synthetic approaches toward

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• biologically active compounds. As an example, we can consider peptide bond formation between an amine and a carboxylic acid. This transformation is a very important reaction in organic synthesis and therefore, many coupling reagents are available on the market [25][26][27][28][29]. Our previous studies have

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

• Jan Geldsetzer and
• Markus Kalesse

Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64

• ′-dimethylethane-1,2-diamine. Keywords: cross coupling; myxobacteria; natural product; ribolactone; Z-enamide; Introduction In the course of our program to provide synthetic access to biologically active natural products we targeted complex polyketides and depsipetides [1][2][3][4][5][6][7][8][9][10]. One

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

• Ming-Xi Bi,
• Shuai Liu,
• Yangen Huang,
• Xiu-Hua Xu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

• , especially those featuring medicinally promising scaffolds. Pyrrolo[1,2-a]indol-3-ones are prevalent scaffolds that widely exist in many bioactive compounds and natural products [17][18][19][20]. Representative examples of biologically active pyrrolo[1,2-a]indol-3-one derivatives are shown in Figure 1

• converted to the mono(trifluoromethylthiolated) products in moderate yields. Further studies on applying radical cascade reactions to the construction of fluorine-containing heterocyclic scaffolds are in progress in our laboratory. Representative examples of biologically active pyrrolo[1,2-a]indol-3-one

Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

• Zhenghui Liu,
• Peng Wang,
• Zhenzhong Yan,
• Suqing Chen,
• Dongkun Yu,
• Xinhui Zhao and
• Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

• preparation of biologically active molecules or their intermediates [28][29]. Generally, aromatic aldehydes are synthesized by Reimer–Tiemann, Gattermann–Koch, Vielsmeier–Haag, or Duff reactions and so forth. Unfortunately, these reactions usually use auxiliary reagents and thus generate large amounts of

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• of biologically active compounds as it imparts a variety of properties such as enhanced binding interaction, metabolic stability, and reaction selectivity by changing physical and chemical properties [23][24][25][26]. Hydrogen bonds (HBs) are associated with highly electronegative atoms (oxygen

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

• Jucleiton J. R. Freitas,
• Queila P. S. B. Freitas,
• Silvia R. C. P. Andrade,
• Juliano C. R. Freitas,
• Roberta A. Oliveira and
• Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

• ; synthesis; Introduction The propargylation of carbonyl compounds is widely used in the synthesis of biologically active natural products [1]. Some examples can be found in the synthesis of histrionicotoxin [2], rhizopodin [3], bafilomycin [4], bryostatin [5], vancosamine [6] and macrolactin A [7]. Although

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

• Thomas J. Cogswell,
• Craig S. Donald and
• Rodolfo Marquez

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

• biologically active compounds. As a result, their synthesis has received extensive research and wide spread publication in the literature [1][2][3][4][5][6]. Dihydropyridinones are an important subclass of heterocycles, which often feature both as useful intermediates, and as interesting species in their own

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

• Sergii Afonin,
• Oleg Babii,
• Aline Reuter,
• Volker Middel,
• Masanari Takamiya,
• Uwe Strähle,
• Igor V. Komarov and
• Anne S. Ulrich

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

• ; membrane-active peptides; photopharmacology; zebrafish embryotoxicity model; Introduction Biologically-active peptides as a class of chemotherapeutic compounds are uniquely positioned between traditional small organic molecule drugs and high-molecular weight biologics [1][2]. Since recent breakthroughs in

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

• Renata Kaczmarek,
• Dariusz Korczyński,
• James R. Green and
• Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

• warranted, which at the same time may provide biologically active compounds. Results and Discussion Preparation of 5-alkynyluridines was carried out from acyl-protected 5-iodouridines (1a,b) [8][63] and the appropriate terminal alkyne in the presence of catalytic amounts of Pd(PPh3)4, copper(I) iodide

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

• Kesatebrhan Haile Asressu and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

• University, Hsinchu 300, Taiwan 10.3762/bjoc.15.295 Abstract Sialic acid-containing glycans are found in different sialic acid forms and a variety of glycosidic linkages in biologically active glycoconjugates. Hence, the preparation of suitably protected sialyl building blocks requires high attention in

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• , Thailand Department of Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand 10.3762/bjoc.15.293 Abstract In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

• Qiao Li,
• Chen Zhuang,
• Donghua Wang,
• Wei Zhang,
• Rongxuan Jia,
• Fengxia Sun,
• Yilin Zhang and
• Yunfei Du

Beilstein J. Org. Chem. 2019, 15, 2958–2965, doi:10.3762/bjoc.15.291

• further applied to the synthesis of the naturally occurring frutinone A. Biologically active chromone derivatives. Methods for the synthesis of chromones via dehydrogenative oxidation of chromanones. Substrate scope studies. Reaction conditions: 1 (1.0 mmol), PhIO (2.0 mmol), DMF (6 mL), rt. Isolated