- Visible Light-Promoted Aryl Azoline Formation over Mesoporous Organosilica as Heterogeneous Photocatalyst
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N-heterocyclic compounds demonstrate wide applications ranging from natural compound production to coordination chemistry. Usually, the synthesis of N-heterocyclic compounds is conducted under thermal conditions, mostly by Lewis acids or metal-containing compounds as molecular catalysts. Here, we report a photocatalytic route for aryl azoline formation by mesoporous organosilica as visible light-active and heterogeneous photocatalyst. Via formation of aromatic aldehydes with various amines, 2-phenyl-2-imidazoline, 2-phenyl-2-oxazoline, 2-phenyl-2-thiazoline and their derivatives could be formed with high conversion and selectivity. Additionally, the organosilica photocatalyst showed high stability and reusability.
- Wei, Wenxin,Li, Run,Huber, Niklas,Kizilsavas, G?nül,Ferguson, Calum T. J.,Landfester, Katharina,Zhang, Kai A. I.
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Read Online
- Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines
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We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami
- Bansal, Shivani,Gupta, Poonam,Halve
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Read Online
- Facile one-pot synthesis of 2-oxazoline
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We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to 5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials.
- Zhu, Jipeng,Zhou, Min,Jiang, Weinan,Zhou, Yang,Song, Gonghua,Liu, Runhui
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supporting information
(2022/01/28)
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- Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies
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A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.
- Atri, Shalu,Bendi, Anjaneyulu,Rao, G. B. Dharma,Raza, Mohd Jamshaiya,Sharma, Nutan
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- Alkyl Chain Length in Poly(2-oxazoline)-Based Amphiphilic Gradient Copolymers Regulates the Delivery of Hydrophobic Molecules: A Case of the Biodistribution and the Photodynamic Activity of the Photosensitizer Hypericin
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Self-assembled nanostructures of amphiphilic gradient copoly(2-oxazoline)s have recently attracted attention as promising delivery systems for the effective delivery of hydrophobic anticancer drugs. In this study, we have investigated the effects of increasing hydrophobic side chain length on the self-assembly of gradient copolymers composed of 2-ethyl-2-oxazoline as the hydrophilic comonomer and various 2-(4-alkyloxyphenyl)-2-oxazolines as hydrophobic comonomers. We show that the size of the formed polymeric nanoparticles depends on the structure of the copolymers. Moreover, the stability and properties of the polymeric assembly can be affected by the loading of hypericin, a promising compound for photodiagnostics and photodynamic therapy (PDT). We have found the limitation that allows rapid or late release of hypericin from polymeric nanoparticles. The nanoparticles entering the cells by endocytosis decreased the hypericin-induced PDT, and the contribution of the passive process (diffusion) increased the probability of a stronger photoeffect. A study of fluorescence pharmacokinetics and biodistribution revealed differences in the release of hypericin from nanoparticles toward the quail chorioallantoic membrane, a preclinical model for in vivo studies, depending on the composition of polymeric nanoparticles. Photodamage induced by PDT in vivo well correlated with the in vitro results. All formulations studied succeeded in targeting hypericin at cancer cells. In conclusion, we demonstrated the promising potential of poly(2-oxazoline)-based gradient copolymers for effective drug delivery and sequential drug release needed for successful photodiagnostics and PDT in cancer therapy.
- Hunto?ová, Veronika,Datta, Shubhashis,Lenkavská, Lenka,Má?Ajová, Mariana,Bil?ík, Boris,Kundeková, Barbora,?avarga, Ivan,Kronek, Juraj,Jutková, Annamária,Mi?kovsky, Pavol,Jancura, Daniel
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p. 4199 - 4216
(2021/10/01)
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- Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones
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The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.
- Liu, Jidan,Yang, Zhenke,Jiang, Jinyuan,Zeng, Qiaohai,Zheng, Liyao,Liu, Zhao-Qing
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supporting information
p. 5927 - 5931
(2021/07/31)
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- Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes
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Transition metal-based anticancer compounds, as an alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp?(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action. This journal is
- Ramos, Robin,Zimbron, Jérémy M.,Thorimbert, Serge,Chamoreau, Lise-Marie,Munier, Annie,Botuha, Candice,Karaiskou, Anthi,Salmain, Michèle,Sobczak-Thépot, Jo?lle
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supporting information
p. 17635 - 17641
(2020/12/30)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones
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We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partner. The present transformation unravels the unusual reactivity of allylic alcohols in the synthesis of 4-
- Singh, Diksha,Kumar, Gangam Srikanth,Kapur, Manmohan
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p. 12881 - 12892
(2019/09/30)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
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A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo
- Kumar, Gangam Srikanth,Khot, Nandkishor Prakash,Kapur, Manmohan
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supporting information
p. 73 - 78
(2018/12/11)
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- Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines
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A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.
- Qiao, Kai,Yuan, Xin,Wan, Li,Zheng, Ming-Wei,Zhang, Dong,Fan, Bing-Bing,Di, Zhe-Chen,Fang, Zheng,Guo, Kai
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supporting information
p. 5789 - 5793
(2017/12/26)
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- Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles
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Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl- and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.
- Gutierrez, David A.,Dean, Dayton R.,Laxamana, Candace M.,Migliozzi-Smith, Madyson,O'Brien, Connor J.,O'Neill, Claire L.,Li, Jie Jack
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p. 261 - 276
(2016/07/06)
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- Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
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The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.
- Mollo, María C.,Orelli, Liliana R.
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supporting information
p. 6116 - 6119
(2016/12/09)
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- A Mild and Regioselective Route to Functionalized Quinazolines
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A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.
- Maiden, Tracy M. M.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.
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p. 14342 - 14346
(2015/10/05)
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- Ruthenium(II) 9,10-phenanthrenequinone thiosemicarbazone complexes: Synthesis, characterization, and catalytic activity towards the reduction as well as condensation of nitriles
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The ligands 9,10-phenanthrenequinone-N4-substituted thiosemicarbazones (HL1-3) and their ruthenium(II) complexes were synthesized and characterized by elemental and spectroscopic methods. The ligands are tridentate, monobasic chelating ligands with O, N, and S as the donor sites and are in the thiol form in all the complexes. Catalytic studies showed that all the complexes displayed good catalytic activity towards the reduction of nitriles and also the condensation of nitriles with 2-aminoalcohol under solvent-free conditions.
- Anitha, Panneerselvam,Viswanathamurthi, Periasamy,Kesavan, Devarayan,Butcher, Ray Jay
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p. 321 - 334
(2015/10/20)
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- Ruthenium(II) 8-quinolinolates: Synthesis, characterization, crystal structure and catalysis in the synthesis of 2-oxazolines
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Abstract New octahedral ruthenium(II) complexes (1-4) have been synthesized from the reaction of ruthenium(II) precursors [RuHCl(CO)(EPh3)3] (E = P or As) with the bidentate Schiff base ligands, 2-((2,6-dimethylphenylimino)methyl)quinolin-8-ol (L1) and 2-((2,6-diisopropylphenylimino)methyl)quinolin-8-ol (L2) in ethanol. These complexes have been characterized by elemental analyses, IR, UV-Vis, 1H, 13C and 31P NMR and ESI-Mass spectroscopy. The molecular structure of the complex [RuCl(CO)(PPh3)2(L2)] (2) was determined by single-crystal X-ray diffraction, which reveals a distorted octahedral geometry around ruthenium(II) ion. The catalytic activity of the new complexes was evaluated for the condensation of nitriles with ethanolamine under solvent free conditions. The processes were operative with aromatic and heteroaromatic nitriles and tolerated several substitutional groups. The studies on the effect of substitution over ligands, coligands, reaction time, temperature and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favorable reaction conditions. A probable mechanism for the catalytic condensation of nitrile has also been proposed. The catalyst was recovered and recycled up to five times without significant loss of its activity.
- Anitha,Manikandan,Prakash,Pachiyappan,Viswanathamurthi,Malecki
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p. 266 - 273
(2015/06/22)
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- Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols
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The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper-NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.
- Trose, Michael,Lazreg, Fa?ma,Lesieur, Mathieu,Cazin, Catherine S. J.
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p. 9910 - 9914
(2015/11/03)
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- An efficient one-pot synthesis of 2-oxazolines with molecular iodine under ultrasound irradiation
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A series of 2-oxazolines were prepared by the condensation of aldehydes with 2-aminoethanol in the presence of molecular iodine and potassium carbonate in t-BuOH at 35-40 °C under ultrasound irradiation. The easy work-up procedure and moderate to good yie
- Xiao, Nan,Wang, Sen Hao,Zhang, Ai Ying,Li, Hong Yang,Wang, Peng,Li, Wei,Chen, Bao Hua,Chen, Guo Feng,Li, Na
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p. 9731 - 9742
(2016/01/12)
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- Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: Synthesis and probe of chiral space
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The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely t
- Herbert, Simon A.,Van Laeren, Laura J.,Castell, Dominic C.,Arnott, Gareth E.
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supporting information
p. 2751 - 2755
(2015/02/19)
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- A mild and efficient synthesis of 2-oxazolines via transamidation- cyclodehydrosulfurisation of thioamides with 2-aminoethanol
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Transamidation of thioamides with 2-aminoethanol, followed by cyclodehydrosulfurisation of the resultant N-(β-hydroxyethyl)thioamides, has been utilised for the mild and efficient synthesis of 2-oxazolines. The developed protocol was found to be of general applicability. Georg Thieme Verlag KG Stuttgart · New York.
- Goud, D. Raghavender,Pathak, Uma
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p. 3678 - 3682
(2013/02/22)
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- A convenient synthesis of 2-oxazolines and 2-benoxazoles with PPh3-DDQ as the dehydrating reagent
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2-Oxazolines and 2-benoxazoles were synthesized in high yields from acylamino alcohols and acylaminophenols, respectively, with triphenylphosphine- 2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DDQ) as the dehydrating and activating reagent. The synthesis was accomplished under neutral conditions.
- Xu, Quancai,Li, Zhengning,Chen, Huiying
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experimental part
p. 925 - 932
(2012/01/03)
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- A powerful palladium-catalyzed multicomponent process for the preparation of oxazolines and benzoxazoles
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Efficient and convenient three-component couplings of an aryl halide, isocyanide, and an amino alcohol under palladium catalysis provide a range of oxazolines and benzoxazoles in excellent yield.
- Boissarie, Patrick J.,Hamilton, Zoe E.,Lang, Stuart,Murphy, John A.,Suckling, Colin J.
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supporting information; experimental part
p. 6256 - 6259
(2012/01/06)
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- Poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′- tetrabromobenzene-1, 3-disulfonamide as new efficient reagents for conversion of alcohols to THP ethers and aldehydes to oxazoline compounds
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This paper is concerned with an easy preparation of THP ethers from primary, secondary and tertiary alcohols and oxazoline compounds from various aldehydes using poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] as new and efficient reagents under ambient conditions without over-oxidation.
- Ghorbani-Vaghei,Akbari-Dadamahaleh,Amiri
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experimental part
p. 301 - 307
(2010/09/03)
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- An exploration of the metal oxide-assisted decomposition and rearrangement of VV-Acyl-1, 3-oxazolidin-2-ones leading to 2-Aryl-2-oxazolines [1]
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An exploration into the utility of the thermally-induced (metal oxide-mediated) CO2 extrusion and subsequent rearrangement of N-acyl-1, 3-oxazolidin-2-ones to form 2-aryl(alkyl)-2-oxazolines is described. The reaction is found to give moderate yields of t
- Deshpande, Ankur A.,Gossage, Robert A.,Jackson, Sarah M.,Quail, J. Wilson,Sadowy, Amber L.,Yadav, Paras N.
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scheme or table
p. 1046 - 1052
(2010/03/01)
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- Preparation of an improved sulfonated carbon-based solid acid as a novel, efficient, and reusable catalyst for chemoselective synthesis of 2-oxazolines and bis-oxazolines
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A highly sulfonated carbon as an efficient, recyclable, nontoxic, and green solid acid catalyst was readily synthesized by simultaneous sulfonation, dehydration, and carbonization of sucrose in sulfuric acid and was characterized by FT-IR, TG-DTG, XRD, and CHNS analysis, neutralization potentiometric titration, and SEM techniques. This new catalyst was used for preparation of 2-oxazolines and bis-oxazolines by reaction of β-aminoethanol with nitriles under reflux conditions. Sonication of this system enhanced the catalytic activity of the carbon-based solid acid and led to higher product yields and shorter reaction times. Another advantage of the system under ultrasonic irradiation is the ability to carry out large-scale reactions. In two cases, the catalyst was reused several times without loss of its activity.
- Mirkhani, Valiollah,Moghadam, Majid,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Mahdavi, Mohammad
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experimental part
p. 1489 - 1494
(2010/07/04)
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- β-Amidoaldehydes via oxazoline hydroformylation
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4-Substituted oxazolines, which are readily synthesized from naturally occurring α-amino acids, are converted efficiently and stereospecifically to β-amidoaldehydes in the presence of synthesis gas and catalytic dicobalt octacarbonyl.
- Laitar, David S.,Kramer, John W.,Whiting, Bryan T.,Lobkovsky, Emil B.,Coates, Geoffrey W.
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supporting information; body text
p. 5704 - 5706
(2010/01/31)
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- An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin
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Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.
- Takahashi, Shogo,Togo, Hideo
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experimental part
p. 2329 - 2332
(2010/03/01)
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- A facile synthesis of 2-oxazolines using a PPh3-DDQ system
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A facile and efficient synthesis of 2-oxazolines from N-(2-hydroxyethyl)amides using a triphenylphosphine-2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DQQ) system is described. The reaction proceeds under neutral and mild conditions, and excellent yields are obtained.
- Xu, Quancai,Li, Zhengning
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experimental part
p. 6838 - 6840
(2010/04/29)
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- Practical reduction of oxazolines to alcohols
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A two-step, one-pot procedure using methyl chloroformate and lithium borohydride was developed to transform 2-substituted-oxazolines into alcohols. This methodology is compatible with a wide range of substrates including heterocyclic, aromatic, and aliphatic functionalized 2-oxazolines. Best results are obtained with electron-rich and ortho substituted 2-aryl-oxazolines.
- Bernardi, Anna,Ouellet, Stéphane G.,Angelaud, Remy,O'Shea, Paul D.
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supporting information; experimental part
p. 6707 - 6708
(2009/04/07)
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- Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene
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An efficient synthesis of 2-substituted oxazolines from aldehydes and 2-amino alcohol using (diacetoxyiodo)benzene as an oxidant, is reported. (Diacetoxyiodo)benzene acts as a mild dehydrogenating agent to convert the initially formed oxazolidine from ald
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.
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p. 1921 - 1924
(2008/03/27)
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- Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
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Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate.
- Ishihara, Midori,Togo, Hideo
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p. 1474 - 1480
(2007/10/03)
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- Preparation and characterization of bicyclic amide acetals and monothioacetals
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We have prepared and characterized new examples of 5-substituted-1-aza-4,6- dioxabicyclo[3.3.0]octanes (bicyclic amide acetals) and examples of the new heterocyclic system, 5-substituted-1-aza-4-oxa-6-thiabicyclo[3.3.0]octanes (bicyclic amide monothioacetals). Detailed analysis of NMR coupling constants and X-ray structure determination for an example of each class of compound established the stereochemistry and conformation of these ring systems.
- Guthrie, J. Peter,Gallant, Roger T.,Jennings, Michael C.
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p. 268 - 278
(2007/10/03)
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- One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols
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The reactions of 1,2- and 1,3-hydroxy azides with aldehydes under acidic conditions were examined. A variety of Lewis acids were examined, of which BF3·OEt2 was found the most convenient. Trimethylsilyl ether derivatives of the alcohols could also be reacted using trimethylsilyl triflate as the promoter. Twenty-five examples that proceed in moderate to quantitative yields are reported.
- Badiang, Jennifer G.,Aube, Jeffrey
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p. 2484 - 2487
(2007/10/03)
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- Reactions of N-Benzyl- and N-Benzylidene-alkanolamines with Bromine: Formation of 1,3-Oxazolidines, 1,3-Oxazinanes, 4,5-Dihydro-1,3-oxazoles and 5,6-Dihydro-4H-1,3-oxazines
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N-Methylbenzylamines react with bromine in acetonitrile to form N-benzylidenemethylamines.Under similar conditions 2-benzylaminoethanols and 3-benzylaminopropan-1-ols afford 3-benzyl-2-phenyl-1,3-oxazolidines and 3-benzyl-2-phenyl-1,3-oxazinanes, respectively. 2-Benzylidineaminoethanols and 3-benzylideneaminopropan-1-ols likewise give 2-aryl-4,5-dihydro-1,3-oxazoles and 2-aryl-5,6-dihydro-4H-1,3-oxazines, respectively.When N-benzylidenemethylamine is treated with bromine in the presence of alcohols, benzaldehyde acetals are obtained.
- Goosen, Andre,McCleland, Cedric W.,Sipamla, Allworth M.
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p. 2221 - 2232
(2007/10/03)
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- Synthesis of 2-Aryl- and 5-Alkyl-2-aryloxazoles from 2-Aryl-5-bromooxazoles
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2-Aryloxazoles, their 5-deuterio derivatives, and 5-alkyl-2-aryloxazoles are prepared in good yields from 2-aryl-5-bromooxazoles via halogen/metal exchange with butyllithium followed by treatment with water, methanol-O-d, or alkyl halides, respectively.
- Kashima, Choji,Arao, Hideki
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p. 873 - 874
(2007/10/02)
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- A New Simple and Mild Synthesis of 2-Substituted 2-Oxazolines
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N-Acylated β-aminoalcohols were converted to 2-oxazolines under very mild conditions employing commonly used phosphorylating reagents.
- Sund, Christian,Ylikoski, Jyrki,Kwiatkowski, Marek
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p. 853 - 854
(2007/10/02)
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- Studies on β-Lactams: Synthesis of Some Penams, Cephams and Their 1-Oxa Analogs
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5,6-Dihydro-4-hydroxy-4-methyl-2-phenyl-1,3-thiazine (1a), after the protection of its hydroxy group with trimethylsilyl chloride, reacts with phenoxyacetyl chloride in the presence of triethylamine to give the hydroxycepham (IIa). 1,3-Oxazines (Ib and Ic
- Sharma, S. D.,Mehra, Usha,Kaur, Sukhjinder
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p. 857 - 859
(2007/10/02)
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