Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• thionyl chloride [27]. These reaction conditions allowed the synthesis of α-brominated fatty acids 5 in a highly selective and efficient manner. Brominated AHL analogues 6a–f (dr 1:1) were prepared in acceptable yields by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)-mediated coupling of the

• ). Synthesis of α-brominated fatty acids 5b–f To a flask equipped with a sodium hydroxide trap the corresponding fatty acid 4 (0.065 mol) and thionyl chloride (5 equiv, 40 mL, 0.325 mol) were added. The reaction mixture was stirred at 50 °C in a water bath. Then, liquid bromine (3 equiv, 5 mL, 0.195 mol) was

• added dropwise and the reaction mixture was stirred under reflux for 6 h and then at room temperature overnight. The excess of thionyl chloride was then removed by distillation. To a beaker containing distilled water in an ice bath, the dark red residue was slowly added and manually stirred. Afterwards

Visible light photoredox-catalyzed deoxygenation of alcohols

• Daniel Rackl,
• Viktor Kais,
• Peter Kreitmeier and
• Oliver Reiser

Beilstein J. Org. Chem. 2014, 10, 2157–2165, doi:10.3762/bjoc.10.223

• produced by thermal dehydration of acetic acid [12], the overall sequence to the benzoylated starting material 6e does not require any type of activation reagents such as thionyl chloride or DCC that are often used for ester formation, but ultimately only requires energy in form of heat. After the

A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand

• Hideki Shimizu,
• Jeffrey C. Holder and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2013, 9, 1637–1642, doi:10.3762/bjoc.9.187

• intermediate, alcohol 4 was reacted with thionyl chloride (Table 2, entries 4–10) to yield chloride 11, which was isolated as the hydrochloric acid salt and dried under vacuum. This compound proved to be bench stable and was spectroscopically unchanged after being left open to oxygen atmosphere and

Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

• Martina Bonsignore,
• Maurizio Benaglia,
• Laura Raimondi,
• Manuel Orlandi and
• Giuseppe Celentano

Beilstein J. Org. Chem. 2013, 9, 633–640, doi:10.3762/bjoc.9.71

• thionyl chloride under reflux for 4 hours. The catalytic efficiency of these catalysts was evaluated in the stereoselective reduction of the N-phenyl imine of acetophenone (Table 2). After running the reaction in dichloromethane at 0 °C for 18 hours, all the catalysts afforded the desired product in

Asymmetric synthesis of host-directed inhibitors of myxoviruses

• Terry W. Moore,
• Kasinath Sana,
• Dan Yan,
• Pahk Thepchatri,
• John M. Ndungu,
• Manohar T. Saindane,
• Mark A. Lockwood,
• Michael G. Natchus,
• Dennis C. Liotta,
• Richard K. Plemper,
• James P. Snyder and
• Aiming Sun

Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23

• excess (>98% ee), we utilized the Mitsunobu reaction of 2-mercaptobenzimidazoles with an amide obtained from (L)-lactic acid (17). Using one equivalent each of 2-mercaptobenzimidazole and α-hydroxyamide 13 (prepared from thionyl chloride-mediated coupling of (L)-lactic acid (17) and 2-chloro-4

• approaches. Preparation of chiral propionamides by HATU-mediated coupling (a) or thionyl chloride-mediated coupling (b). In vitro screening of analogues of 1. Antiviral potencies and solubilities for 1 and analogues. Supporting Information Contains detailed synthetic procedures and characterization data for

Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

• Miroslav Murár,
• Gabriela Addová and
• Andrej Boháč

Beilstein J. Org. Chem. 2013, 9, 173–179, doi:10.3762/bjoc.9.20

• sodium salt C was subsequently converted to the hydrochloride salt of 3-amino-4-hydroxybenzene-1-sulfonyl chloride (D) by treatment with thionyl chloride at room temperature. The amino group of D was protected in the form of a 2-methylbenzo[d]oxazole-5-sulfonyl chloride (E) by reaction of D with (EtO)3CH

The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

• Francesco Airaghi,
• Andrea Fiorati,
• Giordano Lesma,
• Manuele Musolino,
• Alessandro Sacchetti and
• Alessandra Silvani

Beilstein J. Org. Chem. 2013, 9, 147–154, doi:10.3762/bjoc.9.17

• troublesome under a wide range of conditions, probably due to the severe steric hindrance of both the amine and acid coupling partners. At the end, acceptable yields could be obtained via formation of the chloride intermediate [48], by reaction of acid 4 with thionyl chloride, and subsequent coupling with 2

Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines – application to a formal synthesis of sarizotan

• Wafa Gati,
• Mohamed M. Rammah,
• Mohamed B. Rammah and
• Gwilherm Evano

Beilstein J. Org. Chem. 2012, 8, 2214–2222, doi:10.3762/bjoc.8.250

• pyridine 16, which was isolated in 61% yield. Further deprotection of the primary alcohol with TBAF followed by chlorination with thionyl chloride finally gave the desired chloromethylpyridine 17, an intermediate used for the preparation of sarizotan 19 at Merck KGaA by coupling of this pyridine fragment

Cyclodextrin-induced host–guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

• Gero Maatz,
• Arkadius Maciollek and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935, doi:10.3762/bjoc.8.224

• degree of functionalization and yield of carboxy-terminated PNIPAM 3. Then, the free carboxy end group was transferred in to the corresponding acid chloride by treatment with thionyl chloride, yielding polymers with a propionyl chloride end group (Scheme 1). The final product 6 was obtained by

• , 6H, CH3). Synthesis of 6. The carboxy-terminated PNIPAM (3, 2 g) was dissolved in 5 mL of dry DMF. To this solution, thionyl chloride (0.15 mL, 2 mmol) and triethylamine (0.28 mL, 2 mmol) were added and stirred for 3 h. The precipitated triethylammonium chloride was filtered and the excess of thionyl

• chloride was removed in vacuum from the DMF-solution. To the obtained solution, triethylamine (0.28 mL, 2mmol) and N,N-dimethyl-[4-(4’-aminophenylazo)phenyl]amine (5, 360 mg, 1.5 mmol) were added and stirred overnight at room temperature. The triethylammonium chloride was filtered off, and the terminated

A novel asymmetric synthesis of cinacalcet hydrochloride

• Veera R. Arava,
• Laxminarasimhulu Gorentla and
• Pramod K. Dubey

Beilstein J. Org. Chem. 2012, 8, 1366–1373, doi:10.3762/bjoc.8.158

• analysis of 8 and 15 in gas chromatography. Both were clearly separated and 15 was absent in 8. The impurity 14 was further structurally assigned by its synthetic preparation starting from 15. The obtained propionic acid 10 was esterified to its methyl ester 11 with methanol and thionyl chloride under

• rt and thionyl chloride (27.28 g, 0.229 mol) was added to this solution at rt. The clear solution was heated under refluxfor 4 h. After completion of the reaction, methanol was distilled off and the remaining reaction mixture was cooled to rt. Then, water (200.0 mL) was added and the pH of the

Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

• Wen-Bin Yi,
• Xin Huang,
• Zijuan Zhang,
• Dian-Rong Zhu,
• Chun Cai and
• Wei Zhang

Beilstein J. Org. Chem. 2012, 8, 1233–1240, doi:10.3762/bjoc.8.138

• determined by chiral phase HPLC analysis on an SHIMADZU LC-20AD system. Synthesis of fluorous quinine ester C-1 Thionyl chloride (1.19 g, 10 mmol) was added to a mixture of (1H,1H,2H,2H-perfluorooctyl)benzoic acid (0.468 g, 1 mmol) and pyridine (75 mg, 1 mmol). After stirring of the mixture for 4 h at 50 °C

• , the reaction container was flushed with nitrogen gas to remove unreacted thionyl chloride. Quinine (0.275 g, 0.85 mmol) and N,N-diisopropylethylamine (129 mg, 1 mmol) in CH2Cl2 (3 mL) was added, and the solution was stirred for 24 h under reflux. After the reaction had been quenched with H2O (2 mL

Photoreactions of cyclic sulfite esters: Evidence for diradical intermediates

• Rick C. White,
• Benny E. Arney Jr. and
• Heiko Ihmels

Beilstein J. Org. Chem. 2012, 8, 1208–1212, doi:10.3762/bjoc.8.134

• glycol sulfite (8) and the hydrobenzoin sulfite (9); and we herein demonstrate that diradical intermediates are generated during the photoextrusion processes. Results and Discussion Styrene glycol sulfite 8 was prepared from thionyl chloride and styrene glycol in the presence of triethylamine [19]. The

• a Büchi 510K and are uncorrected. Phenyl benzyl ketone, diphenyl acetaldehyde, diphenylmethane, benzil, phenyl acetaldehyde, and bibenzyl were obtained commercially (Aldrich) and used as received. Styrene glycol sulfite was prepared by adding thionyl chloride (2.5 g, 21 mmol) in diethyl ether (50 mL

• 7.5 (5H). meso-Hydrobenzoin sulfite. Thionyl chloride (1.7 g, 14 mmol) in diethyl ether was added dropwise to a solution of meso-hydrobenzoin (2.1 g, 10 mmol) and triethyl amine, 2.5 g (25 mmol) in ether (100 mL). After being stirred for 3 h, the mixture was poured into water (100 mL), the ether layer

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

• economic synthetic route, renders scaffold 37 as a promising platform for further rational drug design. Synthesis Treatment of dicarboxylic acids 34a–c by a standard method [36] using thionyl chloride and 1H-benzotriazole gave the corresponding benzotriazole derivatives in 37–54% yield (Scheme 1, see

Synthesis of functionalized macrocyclic derivatives of trioxabicyclo[3.3.0]nonadiene

• Sabine Leber,
• Gert Kollenz and
• Curt Wentrup

Beilstein J. Org. Chem. 2012, 8, 738–743, doi:10.3762/bjoc.8.83

• dipivaloylketene (1), which slowly dimerizes to the dimeric oxoketene 2 at room temperature [2][3]. Hydrolysis and subsequent chlorination with thionyl chloride afforded the bisdioxine diacid dichloride 3 [3]. 4,4’-(2-Nitro-1,4-phenylene)bis(4-oxabutanol) (7): Diol 6 was prepared according to the literature [18

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

• , 248.104859; found, 248.104835 + 0.96 ppm. 1,2,3,4-Tetrahydroazulene-2,6-dicarboxylic acid 2-(4-cyanophenyl) ester 6-ethyl ester (9): Thionyl chloride (0.021 mL, 0.28 mmol) was added to a solution of 4-(N,N-dimethylamino)pyridine (34 mg, 0.27 mmol) in dichloromethane (5 mL) at −20 °C. Acid 8 (70 mg, 0.28 mmol

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Armin de Meijere and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

• acid provided the dichloroisothiazolocarboxylic acid 18 [24], which could be easily converted with thionyl chloride to the corresponding acid chloride 19 (93% yield). The latter smoothly reacted with the azabicyclohexane derivatives 1 and 2 to provide the corresponding amides 20 and 21, respectively

Perhydroazulene-based liquid-crystalline materials with smectic phases

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

Beilstein J. Org. Chem. 2012, 8, 403–410, doi:10.3762/bjoc.8.44

• -8a), 42.48 (2 × t, C-1, C-3), 45.60 (d, C-6), 182.54 (s, C=O); MS (EI, 70 eV) m/z (%): 294 (36) [M+], 276 (14) [M+ − H2O], 265 (26) [M+ − C2H5], 181 (54) [M+ − C8H17], 179 (100) [181 − H2], 133 (52) [179 − H2CO2]. General procedure for esterification of 8a, 8b and 10a, 10b. Thionyl chloride (0.021 mL

Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties

• Antonio Avellaneda,
• Courtney A. Hollis,
• Xin He and
• Christopher J. Sumby

Beilstein J. Org. Chem. 2012, 8, 71–80, doi:10.3762/bjoc.8.7

• 11 using thionyl chloride [35][36]. Initial attempts to synthesise 3 using the standard procedure [15][16] were unsuccessful. In fact, the far greater acidity of 11 (compared to 6 or 4,4’-dicyanodiphenylmethane) allowed the use of sodium hydride instead of n-butyllithium as a base in the synthesis of

Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit

• Jens Eckelmann,
• Vittorio Saggiomo,
• Svenja Fischmann and
• Ulrich Lüning

Beilstein J. Org. Chem. 2012, 8, 11–17, doi:10.3762/bjoc.8.2

• experiments are under investigation. Experimental General remarks All reagents were obtained from commercial sources and used without additional purification unless otherwise indicated. 5-tert-Butylisophthaloyl dichloride (3) was prepared from 5-tert-butylisophthalic acid and thionyl chloride according to

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• ice, acidified with HCl and recrystallized from ethanol [22]. 6,8-Diiodocoumarin-3-carbonyl chloride (3). Compound 2 (0.44 g, 10 mmol) was dissolved in dry benzene (40 mL), 2 mL of thionyl chloride was added and the solution was refluxed for 1 h. A few drops of formic acid were added to eliminate the

• unreacted thionyl chloride, and the solvent was removed under reduced pressure. The solid obtained was recrystallized from benzene. Yellow crystals: Yield 92%; mp 180 °C; Anal. calcd for C10H3ClI2O3: C, 26.10; H, 0.65; found: C, 26.11; H, 0.67; IR (KBr, cm–1): 3055 (C–H aromatic), 1774, 1718 (2 CO); 1H NMR

Synthesis of enantiomerically enriched (R)-¹³C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine

• Stephen P. Fletcher,
• Jordi Solà,
• Dean Holt,
• Robert A. Brown and
• Jonathan Clayden

Beilstein J. Org. Chem. 2011, 7, 1304–1309, doi:10.3762/bjoc.7.152

• less hindered conformer of 3. Alkylated 5 was freed from its protecting group and the naphthamide “aide-mémoire” by heating to reflux in 47% hydrobromic acid, followed by esterification with methanol and thionyl chloride, which returned the labelled Aib as its methyl ester hydrochloride salt 6* in 93

• thionyl chloride (2 mL) were added and the reaction mixture heated to reflux for 1 h. The reaction mixture was concentrated, and excess SOCl2 was removed by adding toluene and concentrating to dryness, giving 6* (400 mg, 93%) as waxy crystals, mp 168–170 °C (dec.) [lit. for unlabelled 6 182–183 °C (dec

Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam

• Václav Jurčík,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2011, 7, 759–766, doi:10.3762/bjoc.7.86

• explored as the enantiomerically pure amine. In the event 4a was generated after aza-Michael addition as a mixture of two stereoisomers, without any obvious diastereoisomeric bias (1:1, 0% de) as judged by both 1H and 19F NMR. β-Lactam ring closure, using thionyl chloride and triethylamine gave the N

• nitrate (CAN) oxidation offered a milder deprotection method [15]. The aza-Michael reaction proved straightforward to generate 4b and then cyclisation again using thionyl chloride and triethylamine gave β-lactams 5b in a 40% de, presumably again a thermodynamically biased isomer ratio. The

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• , India. Thionyl chloride, 3-aminopyridine, methyl iodide were purchased from Spectrochem, India. D2O, DMSO-d6 and CDCl3 were obtained from Aldrich Chemical Co. Thin layer chromatography was performed on Merck pre-coated silica gel 60-F254 plates. All the material used in the cell culture study, such as

• acid (3 g) was refluxed with thionyl chloride (1 mL) for 4 h in an oil bath at 70 °C. The unreacted thionyl chloride was removed with a rotary-evaporator. The resulting compound (90% yield) was dissolved in dry dichloromethane (DCM) and then 3-aminopyridine (1.5 equiv dissolved in minimum quantity of

Synthesis and crossover reaction of TEMPO containing block copolymer via ROMP

• Olubummo Adekunle,
• Susanne Tanner and
• Wolfgang H. Binder

Beilstein J. Org. Chem. 2010, 6, No. 59, doi:10.3762/bjoc.6.59

• synthesis of norbornene monomers 7 and 9 were obtained from Sigma-Aldrich Chemical Co. (Germany) and used as received without further purification unless otherwise indicated. Bicyclopentadiene (100%), fumaric acid (99+%), thionyl chloride (99+%, Fluka), pyridine (99.8%), methanol and 4-hydroxy-2,2,6,6