Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• accompanied with simultaneous phosphorylation [42] (Scheme 19). The particular importance of this economic and highly efficient synthetic method is the complementarity of the starting material, the easy availability of 2-isocyanobiphenyls, which could be converted to variously substituted phenanthridines in

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• that we succeeded in the selective synthesis of 8 and 9 by simply changing the reaction solvent. We next applied this synthetic method to other π-conjugated guests. Scheme 3 shows the synthetic routes to precursor of PM β-CD based insulated oligothiophene. Mono-6-desmethyl PM β-CD alcohol 10 was

Synthesis of graft polyrotaxane by simultaneous capping of backbone and grafting from rings of pseudo-polyrotaxane

• Kazuaki Kato,
• Katsunari Inoue,
• Masabumi Kudo and
• Kohzo Ito

Beilstein J. Org. Chem. 2014, 10, 2573–2579, doi:10.3762/bjoc.10.269

• previously reported GPR, whereas the solubility of the GPR with short or sparse chains obtained in run 1 was not significantly different from that of PR without graft chains. Toward that end, we successfully simplified the synthesis of GPR. Conclusion We demonstrated a novel synthetic method toward GPRs

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions “on water” instead of hazardous oxidant reagents currently employed in aqueous alcoholic media. Keywords: 1,4-naphthoquinone monoimines; on water; oxidative coupling; rose bengal; solar

Total synthesis of the proposed structure of astakolactin

• Takayuki Tonoi,
• Keisuke Mameda,
• Moe Fujishiro,
• Yutaka Yoshinaga and
• Isamu Shiina

Beilstein J. Org. Chem. 2014, 10, 2421–2427, doi:10.3762/bjoc.10.252

• already developed the synthetic method of lactones with various ring sizes using 2-methyl-6-nitrobenzoic anhydride (MNBA) under mild reaction conditions in the presence of a nucleophilic catalyst such as 4-(dimethylamino)pyridine (DMAP) [25][26]. By using this method, we have demonstrated that unusual

One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S_N2 reaction

• Yiwen Xiong,
• Ping Qian,
• Chenhui Cao,
• Haibo Mei,
• Jianlin Han,
• Guigen Li and
• Yi Pan

Beilstein J. Org. Chem. 2014, 10, 1802–1807, doi:10.3762/bjoc.10.189

• with 1a as a model substrate to fully explore this new synthetic method (Table 1). Diamine product 5a was obtained in 83% yield when 1a reacted with benzylamine in acetonitrile at room temperature for 0.5 h (Table 1, entry 1). Increasing the temperature to 50 °C, gave no improvement on the yield (Table

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp²)–H activation/C–O formation

• Seohyun Shin,
• Dongjin Kang,
• Woo Hyung Jeon and
• Phil Ho Lee

Beilstein J. Org. Chem. 2014, 10, 1220–1227, doi:10.3762/bjoc.10.120

• -catalyzed C(sp2 and sp3)–H activation/C–O formation [42]. In this context, we herein report the synthetic method of alkoxy dibenzooxaphosphorin oxides from 2-(aryl)arylphosphonic acid monoesters via Pd-catalyzed C(sp2)–H activation/C–O formation (Scheme 1). Results and Discussion First, a wide range of 2

• ], resulting in the formation of palladacycle III. Thereafter, ethoxy dibenzooxaphosphorin oxide 2a is obtained from the oxidation of the Pd(II) to Pd(IV) species IV and the subsequent C–O reductive elimination. Conclusion In this paper, we have developed an efficient synthetic method for a wide range of

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• of the oligomer chain (Figure 2) depended on the utilized synthetic method. We found that the MorGly oligomers containing the residues of type A formed less stable complementary complexes than oligomers containing residues of type B. Another interesting fact demonstrated in the article [20] was the

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

• Hannes Mikula,
• Julia Weber,
• Dennis Svatunek,
• Philipp Skrinjar,
• Gerhard Adam,
• Rudolf Krska,
• Christian Hametner and
• Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

• -glucoside than ZEN-14-glucoside in barley roots [17]. We therefore intended to develop a synthetic method for regiocontrolled conjugation of ZEN. Basically, the RAL type moiety of ZEN contains two possible sites for glycosylation/sulfation, but due to the higher reactivity of the phenol group at position 14

Regioselective S_N2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

• Silong Xu,
• Jian Shang,
• Junjie Zhang and
• Yuhai Tang

Beilstein J. Org. Chem. 2014, 10, 990–995, doi:10.3762/bjoc.10.98

• SN2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine as an efficient synthetic method for α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction features additional advantages as mild conditions

Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen

• Hiroki Moriwaki,
• Daniel Resch,
• Hengguang Li,
• Iwao Ojima,
• Ryosuke Takeda,
• José Luis Aceña and
• Vadim A. Soloshonok

Beilstein J. Org. Chem. 2014, 10, 442–448, doi:10.3762/bjoc.10.41

• adjusting stoichiometry or developing catalytic reactions to achieve a specific chemical and stereochemical outcome [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. On the other hand, a measure of the value of a synthetic method, regardless of its

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• symmetric isomer of the 1,3,5-trisubstituted benzene was not detected, and the yield of the 1,2,4-trisubstituted isomer was almost quantitative. Therefore, we came to the conclusion that this synthetic method and the following purification procedures supplied the 1,2,4-trisubstituted benzene-cored DLC

• the central benzene core have important impacts on the supramolecular packing and phase-transition temperature. We anticipate that this Co2(CO)8-catalyzed synthetic method can be used for the synthesis of liquid crystalline polymer networks. Experimental Instruments and conditions: See Supporting

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

• Santos Fustero,
• Paula Bello,
• Javier Miró,
• María Sánchez-Roselló,
• Günter Haufe and
• Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

• group, which involved the use of 1,7-octadiene as an internal source of ethylene. Keywords: cross metathesis; Diels–Alder; one-pot reaction; organo-fluorine; propargylic difluorides; Introduction In recent years the number of applications of olefin metathesis as a mild and competitive synthetic method

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the

A reductive coupling strategy towards ripostatin A

• Kristin D. Schleicher and
• Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

• Prusov extended their synthetic method to syntheses of 15-deoxyripostatin A, and later ripostatin A itself [9]. All of these approaches to the ripostatins share several key features: use of ring-closing metathesis to form the 14-membered macrocycle, preceded by one or more Stille couplings to generate

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• its simple chemical structure, controlled synthetic method, reasonable spectral absorption, good semiconducting properties, high chemical stability, and wide commercial availability. Its emergence as a semiconducting material came with the development of synthetic methods that enable production of

Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates

• Loránd Kiss,
• Melinda Nonn,
• Reijo Sillanpää,
• Santos Fustero and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1164–1169, doi:10.3762/bjoc.9.130

• ][60], only a relatively small number of fluorinated derivatives of this class of compounds have been synthesized so far [61][62][63][64][65][66][67][68][69][70]. Results and Discussion We recently developed a synthetic method for the regio- and stereoselective introduction of a fluorine atom onto the

Efficient synthesis of β’-amino-α,β-unsaturated ketones

• Isabelle Abrunhosa-Thomas,
• Aurélie Plas,
• Nishanth Kandepedu,
• Pierre Chalard and
• Yves Troin

Beilstein J. Org. Chem. 2013, 9, 486–495, doi:10.3762/bjoc.9.52

• synthetic method to the preparation of piperidine natural products. Experimental Organic solutions were dried over MgSO4 or Na2SO4, and filtered. When anhydrous solvents were used, they were prepared as follows: tetrahydrofuran (THF) was distilled under N2 from sodium benzophenone ketyl and used immediately

A new synthetic protocol for coumarin amino acid

• Xinyi Xu,
• Xiaosong Hu and
• Jiangyun Wang

Beilstein J. Org. Chem. 2013, 9, 254–259, doi:10.3762/bjoc.9.30

• and relatively easy to prepare this kind of fluorescent amino acid with the new synthetic method. Furthermore, it can be applied to synthesize other derivatives of the coumarin amino acid with some specific properties. Keywords: coumarin; fluorescent probe; halogen derivatives; non-natural amino acid

N-Heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed Mizoroki–Heck reaction of aryl chlorides with styrenes

• Ting-Ting Gao,
• Ai-Ping Jin and
• Li-Xiong Shao

Beilstein J. Org. Chem. 2012, 8, 1916–1919, doi:10.3762/bjoc.8.222

• ) as the ionic liquid. Keywords: aryl chloride; Mizoroki–Heck reaction; N-heterocyclic carbene; palladium complex; synthetic method; Introduction The palladium-catalyzed reaction between organic halides and alkenes, the Mizoroki–Heck reaction, is one of the most versatile methods for the formation of

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• more efficient synthetic method for the stereoselective allylation of 4 using an appropriate combination of allylic reagent and Lewis acid to produce the desired diastereomer 7 preferentially. Beginning with a reaction employing indium chloride (InCl3) instead of TBSOTf at 0 °C in dichloromethane, we

Synthesis of axially chiral oxazoline–carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

• Feijun Wang,
• Shengke Li,
• Mingliang Qu,
• Mei-Xin Zhao,
• Lian-Jun Liu and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 726–731, doi:10.3762/bjoc.8.81

• amide 14a as a mixture of diastereomeric isomers successfully in 91% yield. To our delight, the two diastereomeric isomers with a chiral N-naphthyl axis, (Sa,S)-15a and (Ra,S)-15a, were synthesized from amide 14a according to the classical synthetic method for the preparation of an oxazoline ring, and

Synthesis of 2,6-disubstituted tetrahydroazulene derivatives

• Zakir Hussain,
• Henning Hopf,
• Khurshid Ayub and
• S. Holger Eichhorn

Beilstein J. Org. Chem. 2012, 8, 693–698, doi:10.3762/bjoc.8.77

• approach was reported previously [5]. Recently, a new synthetic method for the construction of a hydroazulene skeleton by a [5 + 2]cycloaddition reaction was also developed [6]. Additionally, there have been many reports on the synthesis of 2,6-disubstituted azulenes [7][8]. In 1951, the ring expansion of

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• synthetic method used to prepare the inorganic species, the presence of coligands (stabilisers) and the surface chemistry of the particular material under investigation. Furthermore, the relative ease and flexibility of synthesis of the organic ligand(s) means that their design is tailored to the particular

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

• Keith Smith,
• Gamal A. El-Hiti,
• Amany S. Hegazy and
• Benson Kariuki

Beilstein J. Org. Chem. 2011, 7, 1219–1227, doi:10.3762/bjoc.7.142

• , not only did 4 cyclize to give 7, but 5 was also in equilibrium with 4, allowing its eventual conversion into 7 and then 8. This fortuitous finding appeared to offer potential as a general synthetic method and the same lithiation procedure was therefore used with a range of other electrophiles