Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• addition of sodium iodide to afford the desired cyclic sulfonamide 54. For the synthesis of (±)-enduracididine (1) and (±)-allo-enduracididine (3), protected (±)-allylglycine 55 was treated with BocNHS(O)2NH2, MgO, Rh2(esp)2 and PhI(OAc)2 in isopropyl acetate followed by sodium iodide to afford cyclic

Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene

• Frederick J. Seidl and
• Noah Z. Burns

Beilstein J. Org. Chem. 2016, 12, 1361–1365, doi:10.3762/bjoc.12.129

• chemoselectively decomposed, via a reductive de-dihalogenation pathway to the corresponding olefin, by heating the crude material to reflux in acetone with sodium iodide. Total synthesis of anverene With scalable access to 6, a total synthesis of (−)-anverene (1) was explored (Scheme 2). Homoprenol (5) was

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• temperature a sample was removed for 1H NMR analysis. This indicated approximately 15% of (E)-60 had been consumed. Enhancing the sluggish reactivity of (E)-60 a catalytic amount of sodium iodide (10 mol %) was added (presumably generating in situ the corresponding allylic iodide). After stirring for a

• in an unoptimized 60% yield and with physicochemical properties similar to those reported [9]. Confident our silver nitrate mediated halide substitution protocol was robust, attention switched to incorporating (Z)-3-methyl-4-chlorobut-2-en-1-ol ((Z)-61). Employing a sodium iodide enhanced reaction

• electrophilic nature of the desired allylic halides (viz. use of allylic chloride and 10 mol % sodium iodide in Scheme 9) we opted to transform 1° alcohols (E)-66 and (Z)-67 into their corresponding allylic bromides (not shown). This was straightforward and efficient using phosphorus tribromide in ether at 0 °C

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

• Kirk W. Shimkin and
• Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

• participated in the reaction, including those bearing esters, ketones, nitro and nitriles (Scheme 18). If the reaction was run in the presence of sodium iodide, vinyl iodides were produced. This protocol is complementary to Hu’s work in that it provides products of trans-carbohalogenation. In an elegant one

A procedure for the preparation and isolation of nucleoside-5’-diphosphates

• Heidi J. Korhonen,
• Hannah L. Bolt and
• David R. W. Hodgson

Beilstein J. Org. Chem. 2015, 11, 469–472, doi:10.3762/bjoc.11.52

• repeatable, we used triethylammonium bicarbonate (TEAB) buffer to control the pH value, and we used ice baths to ensure constant conditions of temperature. Owing to its charge-dense nature, we hoped to be able to precipitate pyrophosphate as its sodium salt through the use of sodium iodide solution in

• acetone, where acetone served as the precipitating solvent. A systematic study of conditions was performed in order to allow selective precipitation of pyrophosphate ions. Variables included; TEAB buffer concentration and volume, the concentration of the sodium iodide solution in acetone and the volume of

• further volumes of sodium iodide solution in acetone. Gratifyingly, the sequence of selective precipitations allowed for the removal of both pyrophosphate and PPN ions, and isolated materials showed high levels of purity, and reasonable levels of mass recovery without chromatographic purifications (Scheme

Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

• Philipp Röse,
• Steffen Emge,
• Jun-ichi Yoshida and
• Gerhard Hilt

Beilstein J. Org. Chem. 2015, 11, 174–183, doi:10.3762/bjoc.11.18

• alcohol functionality takes place. It is mentionable that under the reaction conditions no aromatic iodination could be observed. Next to sodium iodide other iodide sources such as KI, I2 or Bu4NI can be used, whereas applying other halogenides such as NaBr, Et4NBr or Bu4NCl led to a complex mixture of

• fiber anode and carbon fiber cathode. Each chamber was charged with 10 mL TBABF4 solution (0.3 M in acetonitrile) and 2,6-lutidine (2.0 equiv). The anodic chamber was charged with the 1,4-diene (1.0 equiv) and sodium iodide (1.1 equiv). Constant current electrolysis (10 mA) was carried out at 0 °C until

• iodoalkoxylated products of type 5 (Scheme 3). The electrolysis was carried out in an H-type divided cell (4G glass filter) equipped with carbon fiber electrodes (see Supporting Information File 1). Each chamber was charged with 2,6-lutidine and TBABF4 in CH3CN (0.3 M) and additionally the 1,4-dienol and sodium

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

• quantitative as it resulted in a mixture of both iodinated and non-iodinated fatty acids. Therefore, α-iodo fatty acids 7a–d were prepared via direct substitution of the corresponding α-bromo fatty acids 5a–d with sodium iodide in 2-butanone [27]. The iodinated AHL analogues 8a–f (dr 1:1) were subsequently

• α-bromo fatty acid 5 (3 mmol) and sodium iodide (2 equiv, 0.90 g, 6 mmol) were dissolved in 10 mL of 2-butanone. The reaction mixture was stirred under reflux for 7 h. Subsequently the solvent was removed under reduced pressure and the brown residue was dissolved in distilled water and subsequently

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• -ketoamides (9a–9j) A mixture of 2,2-dibromo-1-phenylethanone (11a, 6.0 g, 21.6 mmol) and sodium iodide (6.48 g, 43.2 mmol) in dimethyl sulfoxide (30.0 mL) at 25–45 °C was stirred for 40–50 minutes. Triethylamine (6.55 g, 64.8 mmol) and tryptamine (10, 3.45 g, 21.6 mmol) were then added to the mixture under a

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

• Jie-Ping Wan,
• Yunfang Lin,
• Kaikai Hu and
• Yunyun Liu

Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25

• recently, it was shown that DHPMs display many new bioactivities such as antioxidation [8], antibacterial [9], antimalaria [10], antimicrobial [11] and sodium iodide symporter inhibition [12], suggesting the great potential of DHPMs in discovering new lead compounds and medicines. Besides their

Use of 3-[¹⁸F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

• Reik Löser,
• Steffen Fischer,
• Achim Hiller,
• Martin Köckerling,
• Uta Funke,
• Aurélie Maisonial,
• Peter Brust and
• Jörg Steinbach

Beilstein J. Org. Chem. 2013, 9, 1002–1011, doi:10.3762/bjoc.9.115

• isolated by distillation in a yield of 24%. Reduction of the amount of sodium iodide from 5 to 1.1 equivalents did not result in a more favourable product distribution. The course of this reaction becomes clear in the light of the pseudohalide concept: the thiocyanate functionality acts as a leaving group

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

• Pechmann condensation [11] from ethyl 4-chloroacetoacetate and resorcinol or its 6-halogenated derivatives (3a, 77.4% yield; 3b, 78.0%; 3c, 70.0%). By suspending compound 3 in triethyl phosphate with a catalytic amount of sodium iodide and heating the mixture under reflux, phosphonate 4 was prepared and

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

• ynones were then treated in situ with sodium iodide and PTSA to yield 2-substituted N-Boc-4-iodopyrroles 32 in good overall yields. Interestingly, this product may be further transformed in situ into the corresponding N-Boc-4-alkynylpyrroles 33 by a further Sonogashira coupling that makes use of the

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

• -vinyl substituted aziridines; ring expansion; sodium iodide; Introduction Vinylaziridines are a particularly interesting class of aziridine derivatives that lend themselves to a host of highly useful synthetic transformations [1]. They are versatile electrophiles and notably undergo regioselective ring

• ring expansion reaction of N-vinyl substituted aziridines was performed under mild conditions by treatment of the aziridines with anhydrous sodium iodide in acetone at room temperature to give 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates 21 in very good to excellent

Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-S-phosphorylacetates

• Milena Trmčić and
• David R. W. Hodgson

Beilstein J. Org. Chem. 2010, 6, 732–741, doi:10.3762/bjoc.6.87

• salt (0.6 g from several chromatographic runs) in water (2.5 mL), and a solution of sodium iodide (0.6 g, 4 mmol) in acetone (12.5 mL). Methanol (2.5 mL) and diethyl ether (2.5 mL) were added to assist precipitation. The mixture was centrifuged at 4500 rpm for 10 min and the supernatant liquid decanted

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• best reactivity. The reaction with sodium iodide to yield CF3I was studied. Compound 27a reacted only when heated, whilst the reactions with 27d and 27e were completed at room temperature after 6 h and 3 h, respectively. For further investigation of trifluoromethylation ability, reagents 27a and 27d (X

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

• analysis. The pure hydrocarbons 2 and 3 were prepared by Diels–Alder reaction of either 7 or 1 [20] with 1,2-bis(dibromomethyl)benzene (8) and sodium iodide to furnish the desired compounds, 2 and 3, in 60 and 40% yield, respectively (Scheme 1 and Scheme 2). During this simple one pot reaction, the sodium

• iodide induces a 1,4-elimination reaction of 8 resulting in the formation of the highly reactive quinodimethane 5,6-bis(bromomethylene)cyclohexa-1,3-diene (9). Diene 9 and the central olefinic double bond of 1 react in a Diels–Alder reaction, followed by a double dehydrobromination, to afford the desired

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

• Markus Nahrwold,
• Arvydas Stončius,
• Anna Penner,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

• were both used a starting materials for diastereoselective alkylation experiments. Attempts to enolise 5 at −78 °C by reaction with NaHMDS or LiHMDS, followed by addition of benzyl bromide did not lead to any alkylation product. Instead, the starting material was re-isolated. Addition of sodium iodide

Shape- persistent macrocycle with intraannular alkyl groups: some structural limits of discotic liquid crystals with an inverted structure

• Sigurd Höger,
• Jill Weber,
• Andreas Leppert and
• Volker Enkelmann

Beilstein J. Org. Chem. 2008, 4, No. 1, doi:10.1186/1860-5397-4-1

• investigation of the Pd-catalyzed dehydrohalogenation is yet not completed, the yield is reproducible higher than with Pd(PPh3)2Cl2, as we reported before [29]. 11 was demethylated with BBr3, the resulting free phenol 12 iodinated with iodine and sodium iodide, and diiodide 13 realkylated with dimethylsulfate