- Arylation of Heterocycles via Rhodium-Catalyzed C-H Bond Functionalization
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(Equation presented) A new method for the rhodium-catalyzed arylation of a variety of heterocycles has been developed. The reaction provided moderate to good yields of the arylated products. A preliminary mechanistic investigation of this reaction revealed the intermediacy of an isolable N-heterocyclic carbene complex.
- Lewis, Jared C.,Wiedemann, Sean H.,Bergman, Robert G.,Ellman, Jonathan A.
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Read Online
- Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
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A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.
- Lin, Zeng-Hui,Tian, Ze-Yu,Zhang, Cheng-Pan
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supporting information
p. 4400 - 4405
(2021/06/27)
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- Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
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Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.
- G?bel, Dominik,Rusch, Pascal,Duvinage, Daniel,Stauch, Tim,Bigall, Nadja-C.,Nachtsheim, Boris J.
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supporting information
p. 14333 - 14355
(2021/10/20)
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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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p. 17635 - 17641
(2020/12/30)
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- Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds
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The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.
- Iyori, Yasuaki,Takahashi, Kenjiro,Yamazaki, Ken,Ano, Yusuke,Chatani, Naoto
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supporting information
p. 13610 - 13613
(2019/11/14)
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- Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
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The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
- G?bel, Dominik,Clamor, Nils,Lork, Enno,Nachtsheim, Boris J.
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supporting information
p. 5373 - 5377
(2019/06/07)
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- Catalytic Alkene Difunctionalization via Imidate Radicals
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The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.
- Nakafuku, Kohki M.,Fosu, Stacy C.,Nagib, David A.
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p. 11202 - 11205
(2018/09/12)
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- Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: Facile synthesis of 1,2-amino alcohols
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A new radical-mediated intramolecular β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.
- Mou, Xue-Qing,Chen, Xiang-Yu,Chen, Gong,He, Gang
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supporting information
p. 515 - 518
(2018/01/19)
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- NH insertion reactions catalyzed by reusable water-soluble ruthenium(II)-hm-phenyloxazoline complex
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A water-soluble Ru(II)-hm-pheox complex was efficiently catalyzed NH insertion of EDA with a broad class of amine derivatives in water/ether biphasic medium to deliver the biologically active precursors α-aminoester products with excellent yields (up to >99%). The products were separated by decantation and the catalyst was washed and reused several times (at least 8 times) without any specific loss of its catalytic activity. The plausible mechanism of the reaction was explained. Additionally, In case of ethylene diamine, the NH insertion product could be transformed to biological active piperazinone compound in high yield. The asymmetric version of this catalytic reaction is under investigation.
- Abu-Elfotoh, Abdel-Moneim
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supporting information
p. 4750 - 4754
(2017/11/29)
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- Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands
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C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides
- Ghorai, Debasish,Müller, Valentin,Keil, Helena,Stalke, Dietmar,Zanoni, Giuseppe,Tkachenko, Boryslav A.,Schreiner, Peter R.,Ackermann, Lutz
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supporting information
p. 3137 - 3141
(2017/09/06)
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- Directed β C-H Amination of Alcohols via Radical Relay Chaperones
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A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.
- Wappes, Ethan A.,Nakafuku, Kohki M.,Nagib, David A.
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supporting information
p. 10204 - 10207
(2017/08/10)
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- Palladium-catalyzed electrophilic C–H fluorination of arenes using oxazoline as a removable directing group
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Dimethyloxazoline was rationally designed to act as a removable ortho-directing group (DG) for the palladium-catalyzed C–H electrophilic fluorination of arenes. Using NFSI as the fluorinating agent, and Pd(II), Ag(I) catalytic system, electrophilic C(sp2–H) ortho-fluorination took place on a variety of aryl substrates to afford the corresponding mono- and di-fluorinated products.
- Gutierrez, David A.,Lee, Wan-Chen Cindy,Shen, Yuning,Li, Jie Jack
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p. 5372 - 5376
(2016/11/11)
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- Hexaalkylguanidinium salts as ionic liquids - Applications in titanium and aluminium alcoholate assisted synthesis
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The solubility of titanium and aluminium alcoholates and of titanium tetrakis(trimethylsilanolate) in several hexaalkylguanidinium-based room temperature ionic liquids was screened. The solvent/solute combinations which displayed the highest alcoholate solubility and stability were applied as Lewis-acidic catalytic media for several dehydrating cyclocondensations: lactamisation of ω-aminocarboxylic acids, direct amidation of carboxylic acids, synthesis of oxazolines from carboxylic acids and 2-aminoethanol, lactonisation of 6-hydroxyhexanoic acid, and Paal-Knorr synthesis of pyrroles.
- Arkhipova, Maria,Eichel, Svetlana,Maas, Gerhard
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p. 56506 - 56517
(2015/02/05)
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- Highly stereoselective Ru(ii)-Pheox catalyzed asymmetric cyclopropanation of terminal olefins with succinimidyl diazoacetate
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The Ru(ii)-Pheox complex is an efficient catalyst for the intermolecular cyclopropanation of various terminal olefins with succinimidyl diazoacetate. This catalytic system can perform under mild conditions, and the desired cyclopropane products are obtain
- Chanthamath, Soda,Phomkeona, Kesiny,Shibatomi, Kazutaka,Iwasa, Seiji
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p. 7750 - 7752
(2012/09/21)
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- Ru(II)-Pheox catalyzed N-H insertion reaction of diazoacetamides: Synthesis of N-substituted α-aminoamides
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An efficient protocol for the preparation of α-aminoamides was developed via the Ru(II)-dm-Pheox catalyzed N-H insertion reaction of various diazoacetamides with several amines, including aniline. This catalytic N-H insertion reaction was also applied to the synthesis of 2-(2-methylquinolin-4- ylamino)-N-phenylacetamide, a potential antileishmanial agent.
- Chanthamath, Soda,Thongjareun, Songkharm,Shibatomi, Kazutaka,Iwasa, Seiji
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p. 4862 - 4865
(2012/09/08)
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- C-H bond arylations and benzylations on oxazol(in)es with a palladium catalyst of a secondary phosphine oxide
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An air-stable, well-defined palladium complex derived from secondary phosphine oxide (SPO) (1-Ad)2P(O)H enabled efficient C-H bond functionalizations with ample scope, which set the stage for direct arylations and benzylations of (benz)oxazoles, as well as unprecedented palladium-catalyzed C-H bond arylations on nonaromatic oxazolines.
- Ackermann, Lutz,Barfuesser, Sebastian,Kornhaass, Christoph,Kapdi, Anant R.
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supporting information; experimental part
p. 3082 - 3085
(2011/08/07)
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- SYNTHESIS OF OXAZOLINE COMPOUNDS
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The present invention provides an improved process for preparing an oxazoline compound of the formula: (I) wherein R1 and R2 are independently hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally sub
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Page/Page column 12
(2010/04/03)
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- A novel and direct synthesis of 1,3,4-oxadiazoles or oxazolines from carboxylic acids using cyanuric chloride/indium
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Direct synthesis of various oxazolines and 1,3,4-oxadiazoles from carboxylic acids was achieved using cyanuric chloride/indium under very mild conditions.
- Kangani, Cyrous O.,Day, Billy W.
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experimental part
p. 5332 - 5335
(2009/12/06)
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- Open vessel mode microwave-assisted synthesis of 2-oxazolines from carboxylic acids
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Microwave-assisted synthesis of 2-oxazolines from carboxylic acids using the open vessel technique is described. This efficient method involves direct condensation of carboxylic acids with excess 2-amino-2-methyl-1-propanol at 170 °C to give the corresponding 2-oxazolines in moderate to excellent yields.
- Sharma, Rishi,Vadivel, Subramanian K.,Duclos Jr., Richard I.,Makriyannis, Alexandros
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experimental part
p. 5780 - 5782
(2009/12/26)
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- Remote C-H bond functionalization reveals the distance-dependent isotope effect
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Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage.
- Li, Jiao-Jie,Giri, Ramesh,Yu, Jin-Quan
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p. 6979 - 6987
(2008/09/21)
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- Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation
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The effects of 3-position substitution of 9-aminomethy 1-9,10- dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2- aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series can bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340 6.52L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.
- Runyon, Scott P.,Mosier, Philip D.,Roth, Bryan L.,Glennon, Richard A.,Westkaemper, Richard B.
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experimental part
p. 6808 - 6828
(2009/10/17)
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- Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: Expanded scope through mechanistic insight
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A practical, functional group tolerant method for the Rh-catalyzed direct arylation of a variety of pharmaceutically important azoles with aryl bromides is described. Many of the successful azole and aryl bromide coupling partners are not compatible with methods for the direct arylation of heterocycles using Pd(O) or Cu(I) catalysts. The readily prepared, low molecular weight ligand, Z-1-tert-butyl-2,3,6,7-tetrahydrophosphepine, which coordinates to Rh in a bidentate P-olefin fashion to provide a highly active yet thermally stable arylation catalyst, is essential to the success of this method. By using the tetrafluoroborate salt of the corresponding phosphonium, the reactions can be assembled outside of a glovebox without purification of reagents or solvent. The reactions are also conducted in THF or dioxane, which greatly simplifies product isolation relative to most other methods for direct arylation of azoles employing high-boiling amide solvents. The reactions are performed with heating in a microwave reactor to obtain excellent product yields in 2 h.
- Lewis, Jared C.,Berman, Ashley M.,Bergman, Robert G.,Ellman, Jonathan A.
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p. 2493 - 2500
(2008/09/18)
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- METHOD FOR PRODUCING 2-OXAZOLINE ANALOGUE OR 1,3-OXAZINE ANALOGUE
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The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an α,α-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R1, R2 and R3 each represents an atom or a group shown in Group 1 to Group 3, and R° represents an atom or a group shown in Group 2 or Group 3. Two or more of R1, R2 and R3 may be bonded to each other to form a ring. Group 1: a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a carboxyl group, a sulfonyl group, a sulfinoyl group or a sulfenyl group; Group 2: an alkyl group, which may have an arbitrary substituent, an aryl group or an aralkyl group; and Group 3: an alkyl-substituted, aryl-substituted or aralkyl-substituted oxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, a thio group, a sulfonyl group, a sulfinoyl group or a sulfenyl group)
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Page/Page column 14
(2008/12/07)
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- Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation
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Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.
- Clayden, Jonathan,Stimson, Christopher C.,Keenan, Martine
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p. 1393 - 1394
(2008/02/03)
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- Efficient oxidative synthesis of 2-oxazolines
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New methodology for the synthesis of variously substituted 2-oxazolines and one dihydrooxazine using aldehydes, amino alcohols, and N-bromosuccinimide as an oxidizing agent is described. This one-pot synthesis is characterized by mild reaction conditions, broad scope, high yields, and its preparative simplicity. Georg Thieme Verlag Stuttgart.
- Schwekendiek, Kirsten,Glorius, Frank
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p. 2996 - 3002
(2008/02/10)
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- An efficient, eco-friendly, one-pot protocol for the synthesis of 2-oxazolines promoted by ionic liquid/indium chloride
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2-Oxazolines have been synthesized using a solventless ionic liquid melt in good yields at ambient temperatures. The efficiency of various Lewis acid catalysts for the same reaction has been compared. The effectiveness of different alkyl chains in the ionic liquids for the synthesis of oxazolines has been studied and a butylmethylimidazolinium chloride/indium chloride melt has been found to be the best media for promoting the reaction. CSIRO 2006.
- Kamakshi,Reddy, Boreddy S.R.
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p. 463 - 467
(2007/10/03)
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- One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent
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A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2,2-dimethyl-1-propanol resulted with excellent yields.
- Kangani, Cyrous O.,Kelley, David E.
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p. 8917 - 8920
(2007/10/03)
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- Facile Syntheses of Oxazolines and Thiazolines with N-Acylbenzotriazoles under Microwave Irradiation
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Microwave reactions of 2-amino-2-methyl-1-propanol (2) or 2-aminoethanethiol hydrochloride (4) with readily available N-acylbenzotriazoles 1a-j in the presence of SOCl2 produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted
- Katritzky, Alan R.,Cai, Chunming,Suzuki, Kazuyuki,Singh, Sandeep K.
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p. 811 - 814
(2007/10/03)
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- The metal-halogen exchange reaction between ortho-substituted aryl halides and Ph2CuLi·LiCN: Scope and applicability for coupling reactions
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Metal-halogen exchange between Ph2CuLi · LiCN and ortho-substituted aryl iodides or bromides may be used to conveniently afford substituted metallated aryls which can subsequently undergo reaction with electrophiles.
- ?etin, Fatma,Bari? ?eno?ul,Gezer, Sibel,Astley, Demet,Astley, Stephen T.
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p. 154 - 157
(2007/10/03)
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- Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide
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Heating N-(β-hydroxyethyl)amides with DIC and Cu(OTf)2 (5 mol %) leads to the formation of 2-oxazolines in good to excellent yields. N-(β-Hydroxy)amides can be cyclised by reaction with diisopropylcarbodiimide (DIC) to give the corresponding 2-
- Crosignani, Stefano,Young, Abigail C.,Linclau, Bruno
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p. 9611 - 9615
(2007/10/03)
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- Solvent-Free Microwave-Assisted Efficient Synthesis of 4,4-Disubstituted 2-Oxazolines
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4,4-Disubstituted 2-oxazolines have been synthesized by a microwave-promoted solvent-free direct condensation of carboxylic acids and disubstituted β-amino alcohols in good to excellent yields. Zinc oxide is a very good solid support in cases where a Lewis acid is required. The method described herein is a very good, safe, clean, economical, and environmentally friendly alternative to the classical procedures. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Garcia-Tellado, Fernando,Loupy, Andre,Petit, Alain,Marrero-Terrero, Alma Leilani
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p. 4387 - 4391
(2007/10/03)
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- Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions
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2-Acyloxy-4,6-dimethoxy-1,3,5-triazines obtained from carboxylic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine were subsequently treated with 2-amino-2-methyl-1-propanol to afford the corresponding 2-oxazolines in excellent yield at room temperature.
- Bandgar,Pandit
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p. 2331 - 2333
(2007/10/03)
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- Oxazoline mediated routes to a unique amino-acid, 4-amino-13-carboxy[2.2]paracyclophane, of planar chirality
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Efficient syntheses leading to 4-amino-13-carboxy[2.2]paracyclophane and derivatives are described. Novel oxazolinyl[2.2]paracyclophanes are used as intermediates and the oxazolinyl and amide groups are shown to be strong ψ-geminal directing groups. Compounds with potential as catalysts have been made. (C) 2000 Elsevier Science Ltd.
- Marchand, Anne,Maxwell, Anderson,Mootoo, Baldwin,Pelter, Andrew,Reid, Alicia
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p. 7331 - 7338
(2007/10/03)
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- Competition in the sodium iodide catalysed isomerisation of some aziridines
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N-Acyl-2,2-dimethylaziridines have been shown to be isomerised by sodium iodide info three isomers. The yield of these isomers appears to depend on the electronic effect of the acyl group.
- Besbes, Neji
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p. 4275 - 4276
(2007/10/03)
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- Natural Kaolinitic clay catalyzed conversion of nitriles to 2-oxazolines
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Natural Kaolinitic clay has been found effective as catalyst in the conversion of aromatic and aliphatic nilriles with 1,2-aminoalcohol to 2-oxazolines (56-96%, yield).
- Jnaneshwara,Deshpande,Lalithambika,Ravindranathan,Bedekar
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p. 459 - 462
(2007/10/03)
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- The direct synthesis of 2-Oxazolines from carboxylic esters using lanthanide chloride as catalyst
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Using catalytic amounts of lanthanide III (Ln = La, Sm) chlorides and amino alkoxides as reagents, an one-pot direct synthesis for 2-oxazolines, in good yield, from carboxylic esters has been developed.
- Zhou, Peiwen,Blubaum, Jason E.,Burns, Christopher T.,Natale, Nicholas R.
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p. 7019 - 7020
(2007/10/03)
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- A facile one stage synthesis of oxazolines under microwave irradiation
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A rapid, high yielding procedure for the synthesis of 2-substituted oxazolines has been achieved under microwave irradiation from alkyl and aryl nitriles and β-amino alcohols using a mild Lewis acid catalyst.
- Clarke, David S.,Wood, Robin
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p. 1335 - 1340
(2007/10/03)
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- BENZ-FUSED LACTONES I. SYNTHESIS OF 3-METHYL-1(3H)-ISOBENZOFURANONES
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Unsubstituted and 3-alkyl substituted 1(3H)-isobenzofuranones are readily prepared in good yields via ortho-metallation of appropriate aromatics.
- Boulet, Camille Andre,Poulton, Gerald Arthur
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p. 405 - 410
(2007/10/02)
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- Reactions of 2-(Tributylstannyl)-4,4-dimethyl-2-oxazoline with Organic Halides. Unusual Product from Aroyl Halide
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2-(Tributylstannyl)-4,4-dimethyl-2-oxazoline (1) reacted with aroyl chloride smoothly without any palladium catalyst to give the unusual product, bis(N-aroyl-4,4-dimethyl-2-oxazolinylidene) in good yields.The reaction of 1 with other types of halide neede
- Kosugi, Masanori,Fukiage, Akio,Takayanagi, Mitsuhiro,Sano, Hiroshi,Migita, Toshihiko,Satoh, Mitsuo
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p. 1351 - 1354
(2007/10/02)
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- Palladium-Catalyzed Coupling of Oxazol-2-yl and 2-Oxazolin-2-yltrimethylstannanes with Aromatic Halides. A New Entry to 2-Aryl and 2-Heteroaryl Oxazoles and Oxazolines
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4-Methyloxazole and 4,4-dimethyl-2-oxazoline were treated with n-butyllithium and trimethyltin chloride to give the corresponding 2-trimethylstannyl derivatives which in the presence of tetrakis(triphenylphosphine)palladium(0) as a catalyst undergo cross-
- Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
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p. 693 - 696
(2007/10/02)
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- CARBON TRANSFER REACTIONS OF Δ2-OXAZOLINIUM AND THIAZOLINIUM CATIONS
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Δ2-Oxazolinium and thiazolinium cations with or without an appendage at any of the heteroatoms transfer their C(2) units at the carboxylic acid oxidation level to binucleophiles and provide the corresponding heterocycles, thus mimicking carbon transfer reactions exhibited by THF models, N-methyl N'-tosyl/acetyl imidazolinium cations.However, these azolinium cations react with phenethylamine and tryptamine to furnish their N-acyl derivatives.
- Singh, Harjit,Sarin, Rakesh
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p. 1449 - 1460
(2007/10/02)
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- Heterocyclic Ring Interchange Reactions
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Δ2-Oxazolinium and thiazolinium cations transfer their C(2) units to acyclic binucleophiles to furnish ring interchange non-aromatic heterocycles.
- Singh, Harjit,Sarin, Rakesh
-
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- MASKED MULTIFUNCTIONALIZATION OF AROMATICS BY PALLADIUM-CATALYZED HALOGEN-OXAZOLINE EXCHANGE
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The (Ph3P)4Pd-catalyzed cross-coupling of aryl and heteroaryl halides with 2-(trimethylstannyl)-4,4-dimethyl-2-oxazoline 3 affords aromatic 2-oxazolines 6 in very high yields.
- Dondoni, Alessandro,Fogagnolo, Marco,Fantin, Giancarlo,Medici, Alessandro,Pedrini, Paola
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p. 5269 - 5270
(2007/10/02)
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- Allenes. Part 44. Formation of Oxazolines and Benzoxazoles from Allenic nitriles and amides and from Phenylpropynenitrile.
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Michael addition of ethanolamines and 2-aminophenol to allenic nitriles, allenic amides and phenylpropynenitrile gives enaminic nitriles and amides which at 290 deg - 320 deg yield oxazolines and benzoxazoles.
- Fomum, Z. Tanee,Nkengfack, A. Ephrem,Mpango, George W. P.,Landor, Stephen R.,Landor, Phyllis D.
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p. 901 - 924
(2007/10/02)
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- The Chemistry of Nitrilium Salts. Part 2. The Preparation of Nitrilium Trifluoromethanesulphonate Salts and Their Reactions with Some Oxygen and Sulphur Nucleophiles
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The syntheses of the nitrilium salts NMe>+3SCF3 i, PhCH2, Ph, CH2=CHCH2, NC(CH2)3, and CH2=CH> by reaction of MeO3SCF3 with the corresponding nitriles are described. the similar reaction between (E)-PhCH=CHCN and MeO3SCF3 gives a mixture of NMe>+SCF3 and the s-triazinium salt 3C3N3H>+3SCF3, which hydrolyzes to give (E)-PhCH=CHCONHMe and the triazine.The compound CF3SO3(CH2)4CN, prepared from I(CH2)4CN and AgO3SCF3, does not form a cyclic nitrilium salt, but slowly dimerizes at room temperature to N(CH2)4CN>+3SCF3.Both I(CH2)4CN and CF3SO3(CH2)4CN can be converted into the salt NMe>+3SCF3, but this does not form a dinitrilium salt on reaction with acetonitrile.On heating benzophenone oxime with CF3SO3H Beckmann rearrangement products are obtained, but conversion of +SCF3 into the nitrilium salt NPh>*3SCF3 ocuurs in only low yield even after 8 h at 130 deg C under high vacuum.The nitrilium salts with R = Ph, Me, Pri, and PhCH2 undergo rapid exothermic reaction with phenol, thiophenol, alcohols, and thiols to give the corresponding imidate and thioimidate salts in high yields. 4,4-Dimethy-2-phenyl-1,3-oxazoline is obtained in 74percent yield on heating NMe>+*3SCF3 with H2NCMe2CH2OH, and both this and 2,4,4-trimethyloxazoline react with MeO3SCF3 to give almoust quantitative yields of the corresponding N-methyloxazolinium salts, which can be reduced to the oxazolidines with NaBH4.N-Methyloxazolinium salts have also been obtained from the reactions of nitrilium salts (R = Ph or Me) with ethylene oxide.
- Booth, Brian L.,Jibodu, Kehinde O.,Proenca, M. Fernanda J. R. P.
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p. 1067 - 1073
(2007/10/02)
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- New Synthesis of 2-Substituted 2-Oxazolines: Transition-Metal-Catalyzed Cross-Coupling of Grignards with 2-(Methylthio)-4,4-dimethyl-2-oxazoline
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A new synthesis of 2-aryl-4,4-dimethyl-2-oxazolines (18a-e) using nickel- and palladium-phosphine complexes to catalyze cross-coupling of Grignard reagents 17 with 2-(methylthio)-4,4-dimethyl-2-oxazoline (16) is described.This reaction represents the firs
- Pridgen, Lendon N.,Killmer, Lewis B.
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p. 5402 - 5404
(2007/10/02)
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