Straightforward Method for the Preparation of Lysine-Based Double-Chained Anionic Surfactants

Double-chained surfactants with potential biocompatibility have been prepared in high yields by lysine acylation with four natural saturated fatty acids (C₆ to C₁₂) and with cis-undec-5-enoic acid. The surfactants were found to assemble into nanotubules in aqueous medium and, when mixed with a commercial cationic surfactant, to spontaneously form liposomes.     

Excellent Synthesis of Adipic Acid

Abstract

A simple, straightforward, and environmentally benign protocol for the synthesis of adipic acid from oxidation of cyclohexanone with Oxone® in the presence of 0.5 mol% RuCl₃ · nH₂O is reported. The reaction completes within a very short time even at room temperature. The generality of the method is shown successfully for synthesis of other C-5 to C-8 dicarboxylic acids.     

Synthesis and Antimicrobial Activity of 1‐[(Substituted Carbamoyl)Amino]‐1H,3H‐1λ5‐[1,3,2]oxazaphospholo[3,4‐a]benzimidazol‐1‐ones

1‐[(Substituted carbamoyl)amino]‐1H,3H‐1λ⁵‐[1,3,2]oxazaphospholo[3,4‐a]benzimidazol‐1‐ones were synthesized by reacting benzimidazole 2‐methanol (4) with different chlorides of carbamidophosphoric acids (3) in the presence of triethylamine at 40–45°C. Their ¹H, ¹³C, and ³¹P NMR spectral data were discussed. The title compounds were tested for their activity against the fungi Aspergillus niger and Fusarium solani and bacteria Staphylococcus aureus and Escherichia coli. These compounds showed moderate antibacterial activity when compared with antifungal activity.     

Organic Reactions in Ionic Liquids: Ionic Liquid Promoted Knoevenagel Condensation of Aromatic Aldehydes with (2‐Thio)Barbituric Acid

Abstract

The Knoevenagel condensation of aromatic aldehydes with (2‐thio)barbituric acid proceeded efficiently in reusable ionic liquids, EAN, BmimBF₄, and BmimPF₆ at room temperature in the absence of any catalyst with high yields.     

Synthesis of Ribavirin Analogues Containing Amino‐Acid Residues

Abstract

A convenient procedure for coupling 1,2,3,5‐tetra‐O‐acetyl‐β‐D‐ribofuranose and 4‐nitroimidazole was developed to obtain β‐anomer as the major product. A novel category of nucleoside analogues with the introduction of natural L‐amino acids to the base moiety were designed and synthesized to develop selective and effective antiviral agents.     

Facile Synthesis of New L‐Arginine Derivatives as Substrates for Trypsin‐Like Proteases

Abstract

Facile and efficient synthetic routes for fluorogenic anilides of L‐arginine have been developed. The amide bond formation uses phosphorous oxychloride as a condensing agent. The synthesis is simple, rapid, and affords excellent yields.     

Regioselective Synthesis of α‐Iodoacetates from Alkenes/Ammonium Acetate/I2 by Woodward's Reaction

Abstract

Regioselective synthesis of α‐iodoacetates from alkenes, ammonium acetate, and iodine in acetic acid is reported. The reaction is facile, fast, environmentally, friendly, and cost effective. α‐Iodoacetates are obtained from both acyclic and cyclic alkenes in high yields ranging from 80–95% within 10–20 min.     

Choline Chloride/Urea Ionic Liquid Catalyzed a Convenient One-Pot Synthesis of Indole-3-propanamide Derivatives

A sequential three-component reaction of aromatic aldehydes with Meldrum's acid and N-methyl indole in the presence of choline chloride/urea ionic liquid as green catalyst has been described. In this one-pot multicomponent reaction, a series of indole-3-propanamide derivatives were synthesized with good to excellent yields. This methodology shows several advantages including fast reaction, easy isolation, operational simplicity that make it a useful and attractive option for the library generation of indole-3-propanamides (5a–l) for drug discovery.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resources: Full experimental and spectral details.]     

Synthesis of poly(l-lactic acid) with improved thermal stability by sulfonic acid-catalyzed melt/solid polycondensation

Melt/solid polycondensation (MP/SSP) is deemed as an alternative synthetic route besides ring-opening polymerization (ROP) in synthesizing poly(l-lactic acid) (PLLA). However, it is found that PLLA synthesized by MP/SSP has much poorer thermal stability than that by ROP due to more residual Sn(II) metallic catalyst in the former, but sulfonic acids does not show any detrimental effect on the thermal stability of PLLA. To synthesizing PLLA with good thermal stability by MP/SSP, a variety of commercially available sulfonic acids were screened as catalysts in MP/SSP of PLLA. Among these nonmetallic catalysts, it was found that 1,3-propanedisulfonic acid (PSA) and 1,5-naphthalene disulfonic acid (NSA) exhibited satisfactory catalytic reactivity and PLLAs with excellent thermal stability, high molecular weight, little coloration and good optical purity were successfully synthesized by MP/SSP. The decomposition temperature was increased by 80–100 °C in comparison to SnCl₂-catalyzed PLLA, and the thermal stability is comparable to commercial PLLA produced by ROP.     

Preparation and Characterization of Styrene/Butyl Acrylate Emulsifier-Free Latex with 2-Acrylamido-2-Methyl Propane Sulfonic Acid as a Reactive Emulsifier

A kind of emulsifier-free latex (FL) was successfully synthesized from styrene (St) and butyl acrylate (BA) with 2-acrylamido-2-methyl propane sulfonic acid (AMPS) as a reactive emulsifier. The particle size of latex particles, stability against electrolytes, minimum film forming temperature (MFT) and water contact angle (CA) were evaluated and compared with a conventional latex (CL). Test results show that FL has larger particle size, better stability against electrolytes and lower MFT value compared with CL; higher AMPS content leads to smaller particle size and smaller water CA.