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

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• biomimicry involved developing synthetic methods to generate complex bioactive natural products. Recent work is attempting to understand how molecular machines operate so their principles can be copied, and learning how to employ biomimetic evolution and learning methods to solve complex problems in science

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• practical synthetic methods for the selective synthesis of precursor dialkynes bearing different substituents (alkyl, aryl) at the triple bonds, based on ketals or an imine as protecting groups. We show for isomeric dialkynes that the reaction cascade induced by Pt(II) includes ring annulation, sulphur

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

• Sushil K. Maurya and
• Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

• synthesis of sugar-embedded glycoconjugates [52][53]. Further, the linear syntheses of macrocycles based on multistep protocols are not cost-effective and the development of efficient, sustainable, greener and economical methods is highly desired. Synthetic methods to produce a diverse collection of

Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

• Yuta Isoda,
• Norihiko Sasaki,
• Kei Kitamura,
• Shuji Takahashi,
• Sujit Manmode,
• Naoko Takeda-Okuda,
• Jun-ichi Tamura,
• Toshiki Nokami and
• Toshiyuki Itoh

Beilstein J. Org. Chem. 2017, 13, 919–924, doi:10.3762/bjoc.13.93

• synthesis of TMG-chitotriomycin (1) initiated from building blocks that were prepared by the degradation of chitin has been reported by Beau [10]; however, practical synthetic methods to provide TMG-chitotriomycin (1) and its derivative in preparative scale are still highly desirable. The automated

DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support

• Johnny N. Naoum,
• Koushik Chandra,
• Dorit Shemesh,
• R. Benny Gerber,
• Chaim Gilon and
• Mattan Hurevich

Beilstein J. Org. Chem. 2017, 13, 806–816, doi:10.3762/bjoc.13.81

• organic chemistry [9][10][11][12][13][14][15][16]. There is a major interest in developing synthetic methods for the preparation of methylated amines and amides [3]. The main challenge in the synthesis of N-methylated amines is to selectively prepare the mono-methylated product and to avoid the formation

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• ], antimicrobial [57][58][59], and specially antibiotic [60][61][62][63][64] agents. Despite their great relevance in drug design, only very few synthetic methods towards these compounds have been reported to date [44]. N-Propargylamines are one of the most specific class of alkynes having diverse reaction

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

• Alejandro Castán,
• Ramón Badorrey,
• José A. Gálvez and
• María D. Díaz-de-Villegas

Beilstein J. Org. Chem. 2017, 13, 612–619, doi:10.3762/bjoc.13.59

• aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved. Keywords: enantioselective synthesis; Michael addition; organocatalysis; pyrrolidines; synthetic methods; Introduction In the first decades of the 21st century, the enantioselective organocatalysis has witnessed a tremendous

Transition-metal-catalyzed synthesis of phenols and aryl thiols

• Yajun Liu,
• Shasha Liu and
• Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

• chemical properties, such as acidity and nucleophilicity, and thus to some extent, the synthetic methods could be developed analogously to each other. In this context, it is valuable to compare their existing synthetic methods for better understanding, so as to inspire organic chemists to invent new

• methods for aryl thiol preparation was not observed. There may be two reasons which block the development of synthetic methods for aryl thiols: (1) Traditionally, sulfur was considered poisonous to transition metal catalysts [93][94]; (2) aryl thiols are very reactive forming intermolecular or

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• .13.48 Abstract This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials

• has never been reviewed in literature and therefore the present work is the first, comprehensive review of synthetic methods and applications of these compounds in medicine and agriculture published from 1926 to 2017. We have divided the review into 4 sections, taking into account the formation of the

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• [9], new and convenient synthetic methods have now emerged. Classical metal dissolving conditions are still used but the method, while it works, shows that the course of the reaction may strongly depend on reaction conditions. The transition-metal-catalyzed defunctionalization reactions cover a wide

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

• Patrick T. Campos,
• Leticia V. Rodrigues,
• Andrei L. Belladona,
• Caroline R. Bender,
• Juliana S. Bitencurt,
• Fernanda A. Rosa,
• Davi F. Back,
• Helio G. Bonacorso,
• Nilo Zanatta,
• Clarissa P. Frizzo and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 257–266, doi:10.3762/bjoc.13.29

• ; quinoxalinone; thiazolo[3,2-a]pyrimidinone; Introduction Various syntheses of polyazaheterocycles are described in the literature because they are important components for the preparation of bioactive molecules [1][2][3]. One of the most important synthetic methods towards compounds containing nitrogen atoms

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• reactions with the advantage of convenient synthetic methods, easy functional group modifications and better stability [37][38][39][40][41][42][43]. Pyridine, azole and imine-based N(sp2) ligands received considerable attention, especially bidentate N,N-ligands. In general, most bidentate N,N(sp2) ligands

A novel method for heterocyclic amide–thioamide transformations

• Walid Fathalla,
• Ibrahim A. I. Ali and
• Pavel Pazdera

Beilstein J. Org. Chem. 2017, 13, 174–181, doi:10.3762/bjoc.13.20

• structure modification of functionalized heterocyclic amides and thioamides [10][11][12][13][14][15][16][17], we found it interesting to design a new convenient and simple method for the thiation of heterocyclic amides. Results and Discussion Many synthetic methods related to thiation of heterocyclic amides

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• research into their bioavailability being conducted, but also into manufacturing techniques that could be utilised for their production. Currently, research into non-solvent based synthetic methods is being pursued to eliminate the influence that the solvent has over the cocrystal formed. Cocrystal

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• derivatives were originally isolated from microorganisms [37][38], e.g., the fosmidomycin [39] is as an antimalarial drug that was isolated from broths of bacteria of the genus Streptomyces [40]. The γ-aminophosphonates were prepared through numerous synthetic methods [41][42][43][44][45]. For instance, they

Catalytic Wittig and aza-Wittig reactions

• Zhiqi Lao and
• Patrick H. Toy

Beilstein J. Org. Chem. 2016, 12, 2577–2587, doi:10.3762/bjoc.12.253

• completed. However, will the research results summarized herein remain merely intellectual achievements or will they become commonly used synthetic methods in the future? Perhaps the answer to this question is how these new reaction systems are viewed from an environmental/green chemistry perspective. In

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

• Ilya V. Efimov,
• Marsel Z. Shafikov,
• Nikolai A. Beliaev,
• Natalia N. Volkova,
• Tetyana V. Beryozkina,
• Wim Dehaen,
• Zhijin Fan,
• Viktoria V. Grishko,
• Gert Lubec,
• Pavel A. Slepukhin and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233

• ). It makes prospective the synthesis of new derivatives of isoxazoles conjugated with other azole rings. The few synthetic methods for 4-(azol-5-yl)isoxazoles published in the literature involve the formation of either azole or isoxazole rings in the final step [1][13][14]. Cyclization reactions of 2

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• friendly procedures. Ball mill assisted syntheses are good alternatives to overcome solubility difficulties in syntheses or isolation of natural compounds from vegetables using CDs [9][10]. Environmentally benign synthetic methods of CD derivatives have been recently reviewed [11]. The key intermediate in

• conditions nor the purifications were optimized in any terms the presented results can serve as starting point to develop more environmentally benign synthetic methods of important CD derivatives. The well-established engineering of HEBM reactions makes them easy to scale-up, while simplified work-up