The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

• Wentao Gao,
• Guihai Lin,
• Yang Li,
• Xiyue Tao,
• Rui Liu and
• Lianjie Sun

Beilstein J. Org. Chem. 2012, 8, 1849–1857, doi:10.3762/bjoc.8.213

• work on the synthesis of hetero-fused quinoline systems that are of interest for medical research. Thus, the aim of the present work is to present the synthesis of novel compounds combining these two bioactive components in a molecular frame work as fused forms. Results and Discussion The synthetic

• methodology developed in our laboratory for the synthesis of a new class of benzoxepino-fused quinoline compounds was achieved in a three-step procedure, commencing with the preparation of ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate (2) as shown in Scheme 1. In fact, from the beginning, we were

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

• Workalemahu M. Berhanu,
• Mohamed A. Ibrahim,
• Girinath G. Pillai,
• Alexander A. Oliferenko,
• Levan Khelashvili,
• Farukh Jabeen,
• Bushra Mirza,
• Farzana Latif Ansari,
• Ihsan ul-Haq,
• Said A. El-Feky and
• Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

• because they are less prone to hydrolysis in vivo and can be synthesized rather inexpensively. The synthetic methodology that has been developed in our lab affords facile assembles of cyclic structures from dicarboxylic building blocks by using a benzotriazole methodology. Seventeen and eighteen-membered

Multistep organic synthesis of modular photosystems

• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2012, 8, 897–904, doi:10.3762/bjoc.8.102

• excellent properties obtained confirm that significant synthetic efforts to build more sophisticated functional systems can be justified and rewarding. In this research, multistep organic synthesis is the means rather than the end. Therefore, the main difference from research dedicated to synthetic

• methodology is that the individual steps often remain unoptimized as long as the level reached is sufficient to produce large enough amounts of the target molecule without extensive effort and cost. However, the quality, timeliness and beauty of the transformations employed are the same, as is the pleasure of

Synthesis and characterization of Sant-75 derivatives as Hedgehog-pathway inhibitors

• Chao Che,
• Song Li,
• Bo Yang,
• Shengchang Xin,
• Zhixiong Yu,
• Taofeng Shao,
• Chuanye Tao,
• Shuo Lin and
• Zhen Yang

Beilstein J. Org. Chem. 2012, 8, 841–849, doi:10.3762/bjoc.8.94

• regions was shown to have a profound effect on the activity. Examples of substituents that impart favorable activity include the alkyl group in region D. By modification of our first generation of synthetic methodology [38], the new general synthesis of the derivatives of Sant-75 is illustrated in Scheme

Syntheses and applications of furanyl-functionalised 2,2’:6’,2’’-terpyridines

• Jérôme Husson and
• Michael Knorr

Beilstein J. Org. Chem. 2012, 8, 379–389, doi:10.3762/bjoc.8.41

• describes the state of the art concerning preparation and applications of such terpyridines bearing a furanyl ring. Review Synthesis by ring closure of 1,5-diketones In 1976, Kröhnke introduced a synthetic methodology to prepare pyridine derivatives that relies on the ring closure of 1,5-diketo-derivatives

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• by the isonitrile function, leading to the ring-close aryloxazol-2-yl palladium complex delivering products after a final reductive elimination step (Scheme 3). Catalytic direct (hetero)arylation of (benz)oxazoles Palladium- and/or copper-catalyzed direct (hetero)arylation with halides: Synthetic

• methodology The first examples of direct C–H heteroarylation of various azoles were reported by Ohta, including the direct C5-selective pyrazinylation of oxazole with chloropyrazines in the presence of Pd(PPh3)4 as catalyst and potassium acetate base (Scheme 4) [36][37]. This protocol was successfully applied

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

• Lukas Hintermann,
• Mauro Perseghini and
• Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

• specifically fluorinated compounds remain difficult to access because of limitations of the synthetic methodology or unpredictable reaction outcomes in the case of fluorinated starting materials. Seebach coined the term “flustrates” for “fluorinated substrates”; a term that also hints at the frustrations

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• -component synthesis has emerged as an important synthetic methodology to gain access to nitrogen-containing structures. The latest developments in this area are discussed in this review. Keywords: amines; multicomponent reactions; palladium; Introduction Nitrogen-containing structures are present in

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S_NAr reaction

• Charlotte Wiles and
• Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

• as the base was investigated as a means of simplifying postreaction processing and reducing the costs associated with the synthetic methodology developed. Using this approach, we investigated the effect of K2CO3 stoichiometry at 195 °C with a reaction time of 30 s, and, as Figure 10 illustrates

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation–decarbonylative alkynylation–cyclocondensation sequences

• Charlotte F. Gers,
• Julia Rosellen,
• Eugen Merkul and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1173–1181, doi:10.3762/bjoc.7.136

• traditional multistep syntheses. Thus, they can be considered to be economically and ecologically efficient [9][10]. In particular, multicomponent syntheses of heterocycles initiated by transition metal catalysis received increasing attention in the past decade [11]. As a one-pot synthetic methodology, this

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

• Jingjing Wu,
• Hui Li and
• Song Cao

Beilstein J. Org. Chem. 2011, 7, 1070–1074, doi:10.3762/bjoc.7.123

• indicated that the reaction proceeded efficiently regardless of reaction conditions, and the Ugi products (5 and 6) were obtained in good yields. The hydrogen atom next to the CF2 group seems to influence the formation of Ugi product. In previous studies, we developed a synthetic methodology to prepare

Continuous gas/liquid–liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination

• Jessica R. Breen,
• Graham Sandford,
• Dmitrii S. Yufit,
• Judith A. K. Howard,
• Jonathan Fray and
• Bhairavi Patel

Beilstein J. Org. Chem. 2011, 7, 1048–1054, doi:10.3762/bjoc.7.120

• complex systems such as fluorinated terpenoids, steroids and a range of heterocyclic systems, upon appropriate synthetic elaboration [7], and, consequently, there is much interest in the development of a synthetic methodology for the preparation of such useful fluorinated intermediates. It has been

• -diketones and hydrazines [23]. However, the synthetic methodology for the preparation of the corresponding fluoropyrazole derivatives has not been developed to any great extent despite the potential use of such systems in life science applications. Recently, we explored direct fluorination of various

Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

• Kiymet Berkil Akar,
• Osman Cakmak,
• Orhan Büyükgüngör and
• Ertan Sahin

Beilstein J. Org. Chem. 2011, 7, 1036–1045, doi:10.3762/bjoc.7.118

• -1,4-dione 28 starting from 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene 6. The most important advantage is the complete selectivity of each reaction step. Although the reactions described follow simple synthetic methodology, the results are quite appealing. The present procedure is particularly

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

• Satish S. More,
• T. Krishna Mohan,
• Y. Sateesh Kumar,
• U. K. Syam Kumar and
• Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

• /bjoc.7.95 Abstract A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2

Recent advances in the development of alkyne metathesis catalysts

• Xian Wu and
• Matthias Tamm

Beilstein J. Org. Chem. 2011, 7, 82–93, doi:10.3762/bjoc.7.12

• metathesis as a tool in organic synthetic methodology [9]. In a very recent report, Finke and Moore reported on the Lewis acid activation of the molybdenum nitrides 26 and 28, which afforded the pre-catalysts 37 and 38 upon addition of one or two equivalents of B(C6F5)3, respectively (Scheme 8) [87]. While

EPR and pulsed ENDOR study of intermediates from reactions of aromatic azides with group 13 metal trichlorides

• Giorgio Bencivenni,
• Riccardo Cesari,
• Daniele Nanni,
• Hassane El Mkami and
• John C. Walton

Beilstein J. Org. Chem. 2010, 6, 713–725, doi:10.3762/bjoc.6.84

• ]. Parallel to that, organic azides are increasingly used as sources of N-centred radicals, although most such methods also require organotin hydrides [17][18][19][20][21][22][23]. In seeking cleaner, less toxic and more efficient synthetic methodology – not reliant on organotin compounds [24][25][26][27][28

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

• Guillaume G. Launay,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 41, doi:10.3762/bjoc.6.41

• limited range of fluorination reagents and methodologies available to synthetic organic chemistry, and novel methods for introducing fluorine into organic molecules continue to be valuable [4]. In this paper we focus on extending the scope of the Prins fluorination reaction as a synthetic methodology. The

Comparison of zwitterionic N-alkylaminomethanesulfonic acids to related compounds in the Good buffer series

• Robert D. Long,
• Newton P. Hilliard Jr,
• Suneel A. Chhatre,
• Tatiana V. Timofeeva,
• Andrey A. Yakovenko,
• Daniel K. Dei and
• Enoch A. Mensah

Beilstein J. Org. Chem. 2010, 6, No. 31, doi:10.3762/bjoc.6.31

• likely explanation for the observed ammonium ion acidity, the possibility of a through space intramolecular interaction (i.e. hydrogen-bonding or similar stabilization) of the proton with the sulfonate moiety cannot be discounted as a contributing factor. Results and Discussion Synthetic methodology

Novel loop-like aromatic compounds: a further step on the road to nanobelts and nanotubes

• Venkataramana Rajuri,
• Dariush Ajami,
• Gaston R. Schaller,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2010, 6, No. 30, doi:10.3762/bjoc.6.30

• characterization of new compounds 2–6 were accomplished. As a common synthetic methodology, the Diels–Alder reaction was applied to 9,9′,10,10′-tetradehydrodianthracene (TDDA) (7) to furnish the [12]annulenes 2 and 3 [16]annulene 6 and adduct 5. Keywords: [n]annulenes; Diels–Alder reaction; nanobelts

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• structure [23][25]. Linear non-naturally-occurring SAA homo-oligomers The first examples of amide-linked SAA-pyranose oligomers were reported as long ago as 1975 by Fuchs and Lehman [26][27]. In 2002, Ichikawa and co-workers developed a synthetic methodology to access oligomers of glycoamino acids, a family

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• species. Note that the peak at −0.8 V is probably due to the reduction of O2 which is difficult to eliminate from the solution. Conclusion In conclusion, we report synthetic methodology based on Ullman coupling to extend the imidazolium aromatic core. From this coupling product we have synthesized and

Synthesis and enzymatic evaluation of 2- and 4-aminothiazole- based inhibitors of neuronal nitric oxide synthase

• Graham R. Lawton,
• Haitao Ji,
• Pavel Martásek,
• Linda J. Roman and
• Richard B. Silverman

Beilstein J. Org. Chem. 2009, 5, No. 28, doi:10.3762/bjoc.5.28

• . Nonetheless, the synthetic methodology is useful for the construction of this ring system. 4-Aminothiazole-based inhibitors with various alkyl groups at the thiazole 5-position could be synthesized, but proved to be unstable in aqueous medium. This is a valuable insight for others contemplating this ring

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring- closing metathesis

• Palakodety Radha Krishna,
• Krishnarao Lopinti and
• K. L. N. Reddy

Beilstein J. Org. Chem. 2009, 5, No. 14, doi:10.3762/bjoc.5.14

• 5,6-dihydropyrone ring of cryptocaryalactone. The advantage of this synthetic methodology is that one can in principle synthesize the other three diastereomers of cryptocaryalactone by altering the Sharpless epoxidation and Carreira’s conditions. Some natural products containing styryl lactones

(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study

• Kazuhiko Nakamura,
• Yu Tachikawa and
• Daisuke Uemura

Beilstein J. Org. Chem. 2009, 5, No. 12, doi:10.3762/bjoc.5.12

• absolute structure of complanine was unambiguously determined by means of synthetic methodology by a “chiral synthon” approach. Related amino alcohols possessing olefins from marine natural resources have been identified [3][4], but synthetic studies of these compounds have not been reported. Results and