β-Hydroxy sulfides and their syntheses

• Mokgethwa B. Marakalala,
• Edwin M. Mmutlane and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

• blockers used in the treatment of hypertension, angina pectoris and some types of cardiac arrhythmia [14]. 3. Synthetic methods to β-hydroxy sulfides β-Hydroxy sulfides are important structural units found in a number of biologically important compounds. Furthermore, they have been used as key

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

• Jiyun Sun,
• Xiaohua Zhen,
• Huaibin Ge,
• Guangtao Zhang,
• Xuechan An and
• Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

• ][13] (Aubagio®, the active metabolite of leflunomide for the treatment of multiple sclerosis), and pleconaril (Figure 1, C) [14][15][16] (an antiviral drug), all possess this privileged substituent. Although many useful synthetic methods [17][18][19][20][21] have been established for introducing the

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• efficient synthetic methods is one of the major goals for future research in chemistry. Perhaps most importantly, the continued interest in troponoids systems originates from the fact that such compounds can be used as both building blocks and starting materials in the synthesis of complex natural products

Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores

• Sang Won Park,
• Soong-Hyun Kim,
• Jaeyoung Song,
• Ga Young Park,
• Darong Kim,
• Tae-Gyu Nam and
• Ki Bum Hong

Beilstein J. Org. Chem. 2018, 14, 1028–1033, doi:10.3762/bjoc.14.89

• of pharmaceutical and medicinal chemistry [6][7][8][9][10][11]. Not surprisingly, the construction of diverse heterocyclic cores including isoxazolines and pyrazolines has garnered much attention from synthetic chemists [12][13][14][15]. Among precedent synthetic methods, the functionalization of

Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

• Felix Scheidt,
• Christian Thiehoff,
• Gülay Yilmaz,
• Stephanie Meyer,
• Constantin G. Daniliuc,
• Gerald Kehr and
• Ryan Gilmour

Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

• ranging from drug delivery through to tissue engineering [3][4]. Collectively, the importance of the 2-oxazoline scaffold for translational research, together with its strategic value in the design of chiral ligands and auxiliaries [5][6][7], has culminated in a rich and innovative arsenal of synthetic

• methods. To contribute to the current catalysis ordnance for the preparation of 2-oxazolines, and provide a direct route to 5-fluoromethyl derivatives from simple unactivated alkenes, the fluorocyclisation of N-allylcarboxamides facilitated by the in situ generation of p-TolIF2 was envisaged [8][9][10][11

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

• Zhensheng Zhao and
• Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

• . Experimental evidence suggests that a radical mechanism is involved. Keywords: allene; chlorination; hypervalent iodine; synthetic methods; vinyl chloride; Introduction Organochlorine compounds are vital as polymer precursors [1], as pharmaceuticals [2][3] and agrochemicals [4][5][6] and as functional

Enzyme-free genetic copying of DNA and RNA sequences

• Marilyne Sosson and
• Clemens Richert

Beilstein J. Org. Chem. 2018, 14, 603–617, doi:10.3762/bjoc.14.47

• was considered a very relevant parameter. We focused on the two classes of activated monomers mentioned above: 2-methylimidazolides and oxyazabenzotriazolides. Synthetic methods for producing such monomers from free nucleotides were briefly reviewed in our earlier account [22]. The methylimidazolides

High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

• Eric Yu,
• Hari P. R. Mangunuru,
• Nakul S. Telang,
• Caleb J. Kong,
• Jenson Verghese,
• Stanley E. Gilliland III,
• Saeed Ahmad,
• Raymond N. Dominey and
• B. Frank Gupton

Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

• , USA 10.3762/bjoc.14.45 Abstract Numerous synthetic methods for the continuous preparation of fine chemicals and active pharmaceutical ingredients (API’s) have been reported in recent years resulting in a dramatic improvement in process efficiencies. Herein we report a highly efficient continuous

• chemistry; hydrogenation; hydroiodic acid; hydroxychloroquine; Introduction Our research group has been focused on the development of new synthetic methods for the preparation of a variety of active pharmaceutical ingredients for global health applications by employing the principles of process

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc

• Kohsuke Aikawa,
• Kohei Yabuuchi,
• Kota Torii and
• Koichi Mikami

Beilstein J. Org. Chem. 2018, 14, 576–582, doi:10.3762/bjoc.14.44

• [1][2]. Therefore, the development of novel synthetic methods for the introduction of fluorinated fragments, such as trifluoromethyl (CF3), difluoromethyl (CF2H), and difluoromethylene (-CF2-), has attracted a great deal of attention from synthetic organic chemists [3][4][5][6]. Among these methods

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• heterocyclic systems. The development of new synthetic routes towards pyrazoloazines for their biological and medicinal exploration is an attractive area for researchers throughout the world. The present review focuses on various synthetic methods developed in the last decade for the synthesis of differently

• , reactions of 5-aminopyrazoles with various reagents to construct a six membered ring with pyrazole are discussed. The synthetic methods have been arranged in order of the ascending number of heteroatoms in the azine ring. The systematic arrangement in this review explores the possibility of providing

• convenient regioselective synthetic methods with mild conditions and good yields of the reactions [40][41]. Aggarwal et al. [42] reported the regiospecific synthesis of 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines 18 by the reaction of 5-aminopyrazole 16 with trifluoromethyl-β-diketones 17 in refluxing

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• minireview mainly focuses on the copper-mediated or -catalyzed trifluoromethylations from 2012 to 2016. And some previous pioneering works were included to gain a comprehensive understanding of the development of the diverse synthetic methods over the time. Throughout this minireview, compounds 1 are the

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage. Keywords: catalysis; deformylation; organic synthesis; organocatalysis; Introduction Imines are extremely versatile intermediates in organic chemistry [1][2][3]. Consequently, many synthetic methods have been developed for the

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

• Azim Ziyaei Halimehjani,
• Martin Dračínský and
• Petr Beier

Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247

• novel dithiocarbamates. Nevertheless, new synthetic methods towards dithiocarbamates are sought after and research in this area is still intense. The introduction of a trifluoromethyl group into organic compounds is a very productive strategy of modification of molecules for various applications in the

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• ; photophysical property; Introduction The chemistry of phospholes, fully unsaturated five-membered heterocyclic rings containing a phosphorus element, has drawn much attention in terms of the development of synthetic methods and elucidation of its spectroscopic properties for applications in organic field

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• are methyl, ethyl, isopropyl or, occasionally, n-butyl [127]. This observation is likely explained by the synthetic methods employed to prepare phosphonates that frequently made use of the Arbuzov reaction [128] involving the commercially available trimethyl, triethyl or triisopropyl phosphite [129

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

• Alexey Yu. Dubovtsev,
• Maksim V. Dmitriev,
• Аndrey N. Maslivets and
• Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

• ; spiro compounds; synthetic methods; Introduction Molecular structures based on partially or exhaustively hydrogenated indole and benzofuran cores are omnipresent in nature. Both types of ring systems are found in a variety of important biologically active natural products [1][2][3][4][5][6][7][8][9][10

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• branching patterns, can indicate the presence and progression of a disease [5][6][7][8][9]. With a better understanding of functions of carbohydrates, the quest for reliable synthetic methods has launched, thus elevating the priority for improving our synthetic competences. The development of new methods

Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

• Hao Wang,
• Cui Chen,
• Weibing Liu and
• Zhibo Zhu

Beilstein J. Org. Chem. 2017, 13, 2023–2027, doi:10.3762/bjoc.13.200

• , which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential

Transition-metal-free synthesis of 3-sulfenylated chromones via KIO₃-catalyzed radical C(sp²)–H sulfenylation

• Yanhui Guo,
• Shanshan Zhong,
• Li Wei and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2017, 13, 2017–2022, doi:10.3762/bjoc.13.199

• the utility of the odorous thiophenols remain as restrictions. In this regard, devising alternative synthetic methods featuring simultaneously the advantages of easily variable, low-cost substrates and operationally practical sulfur sources is highly demanding. Herein, we report a new synthetic

Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al₂O₃/MeSO₃H

• Hashem Sharghi,
• Mahdi Aberi,
• Mohsen Khataminejad and
• Pezhman Shiri

Beilstein J. Org. Chem. 2017, 13, 1977–1981, doi:10.3762/bjoc.13.193

• MeSO3H has been previously used as an effective and mild reagent for organic transformations [14]. In continuation of our studies to develop new synthetic methods for heterocycles [15][16][17][18][19], herein, we disclose a novel route to the synthesis of 3-arylquinolines from aniline derivatives and

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• isolate up to 77% of differently substituted indole derivatives (Scheme 55). Advantages and limitations Over a couple of decades the area of mechanochemistry considered to be one of the best solvent-free synthetic methods. This area has become significantly interesting to chemists due to its benefits over

Solvent-free sonochemistry: Sonochemical organic synthesis in the absence of a liquid medium

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 1850–1856, doi:10.3762/bjoc.13.179

• synthetic methods (see Supporting Information File 1). A control experiment was carried out, whereby the reagents were mixed as two solids and left under ambient temperature and pressure for several weeks, after three weeks, a conversion of 72% to the desired product was observed, confirming the advantage

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• proteins against the activity of proteolytic enzymes [6][7], or are precursors of numerous active compounds such as β-lactams [8][9]. Finally, β-amino acids are present in numerous natural products [10]. These properties have generated great interest in the development of synthetic methods for the

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

• Carolina S. García,
• Paula M. Uberman and
• Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

• . Among them, cross-coupling and coupling reactions have been broadly applied for C–C and C–heteroatom bond formation [1][2][3][4][5][6]. These reactions have been proven to be powerful and attractive synthetic methods due to their high selectivity and tolerance to a wide range of functional groups on

• other hand, and in order to further explore the scope of the PVP-Pd NPs catalyst, the synthesis of stilbene derivatives by Pd-tandem reactions was carried out. Some synthetic methods employing consecutive Pd Hiyama–Heck coupling reactions have been reported to obtain a variety of stilbene derivatives

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• particular, 2,4,5-trisubstituted oxazoles attract attention as pharmacologically potent scaffolds because structural diversity can be efficiently generated by the introduction of a variety of substituents. Accordingly, numerous synthetic methods have been developed and can be roughly classified into three