- Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
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A selective ortho,ortho’-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.
- Hess,Guelen,Alandini,Mourati,Guersoy,Knochel
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supporting information
(2021/12/06)
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- COMPOUNDS
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The invention relates to novel compounds for use as inhibitors of NLRP3 inflammasone production, wherein such compounds are as defined by compounds of formula (I) and wherein the integers R1, R2 and R3 are defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of a disease or disorder that is associated with NLRP3 inflammasome activity.
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Page/Page column 52; 85
(2021/12/08)
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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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- Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes
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A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.
- Liu, Can,Wang, Zhiming,Wang, Lei,Li, Pinhua,Zhang, Yicheng
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p. 9209 - 9216
(2019/11/05)
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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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- Synthesis of asymmetrically disubstituted anthracenes
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We have developed synthetic pathways toward differently substituted hydroxyanthracenes (anthrols) with the aim to investigate their photochemical reactivity in dehydration reactions. Although the syntheses of anthracenes substituted at positions 9,10 are well known, reports for the synthesis of anthracenes with different substitution patterns are scarce. Herein we review known and report novel synthetic pathways toward anthrols with substituents at 1,2-, 2,3-, and 2,6- positions. We present two synthetic approaches: (i) building of the anthracene tricyclic fused ring system from the appropriate benzene derivatives, and (ii) reduction of the corresponding anthraquinones. Reduction of 2-hydroxyanthracene-1-carbaldehyde to the corresponding alcohol yields rather unexpected 1,1′-methylenedianthracen-2-ol, whose proposed mechanism of formation is supported by experimental observations and calculations.
- ?kalamera, ?ani,Veljkovi?, Jelena,Pti?ek, Lucija,Sambol, Matija,Mlinari?-Majerski, Kata,Basari?, Nikola
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supporting information
p. 5892 - 5899
(2017/09/09)
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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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- 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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supporting information
p. 5372 - 5376
(2016/11/11)
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- Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature
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Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. Copper light: Room-temperature C-H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.
- Yang, Fanzhi,Koeller, Julian,Ackermann, Lutz
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supporting information
p. 4759 - 4762
(2016/04/19)
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- Zincation of 4,4-dimethyloxazoline using TMPZnCl·LiCl. A new preparation of 2-aryloxazolines
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The metalation of 4,4-dimethyloxazoline using TMPZnCl·LiCl provides a stable 2-zincated oxazolinyl reagent which readily undergoes palladium-catalyzed Negishi cross-couplings allowing a new access to 2-aryloxazolines. Cu-mediated acylation and allylation reactions also proceed in good yields. This journal is
- Haas, Diana,Hofmayer, Maximilian S.,Bresser, Tomke,Knochel, Paul
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supporting information
p. 6415 - 6417
(2015/04/14)
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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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- Ortho-directed functionalization of arenes using magnesate bases
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Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.
- Bellamy, Estelle,Bayh, Omar,Hoarau, Christophe,Trecourt, Francois,Queguiner, Guy,Marsais, Francis
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supporting information; experimental part
p. 7043 - 7045
(2010/11/02)
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- Spiro compounds
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Compounds of the general formula (I): wherein Ar1represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.
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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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- 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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- Flavonoid derivatives as organometallic bioprobes
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The synthesis of organoiron derivatives of biologically active flavonoids is described. Lithium enolates of functionalised protected acetophenones and metallated derivatives of substituted aromatic rings have been employed as nucleophiles in combination with tricarbonyl(η5-cyclohexadienyl)iron electrophiles. Products have been converted into flavonoid and chalcone derivatives. Enolates generated from protected flavanones have also been used in nucleophile addition reactions, and a one-pot in situ protection, nucleophile addition, deprotection sequence is reported.
- Anson, Christopher E.,Creaser, Colin S.,Malkov, Andrej V.,Mojovic, Ljubica,Stephenson, G. Richard
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p. 101 - 122
(2007/10/03)
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- Pd(OAc)2/2-aryl-2-oxazolines catalyzed Suzuki coupling reactions of aryl bromides and arylboronic acids
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A series of 2-aryl-2-oxazolines were prepared and examined as ligands for the Suzuki coupling reaction of aryl bromides and arylboronic acids. 2,2′-(1,3-Phenylene)bisoxazoline/Pd(OAc)2 was found to be an efficient catalyst for a variety of substrates to afford the coupling products in good to excellent yields.
- Tao, Bin,Boykin, David W
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p. 4955 - 4957
(2007/10/03)
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- Novel spiro compounds
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Compounds of the general formula (I): wherein Ar1 represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.
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- Spiro compounds
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Spiro compounds of the general formula (I): wherein Ar1represents an optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W each represent a nitrogen atom or an optionally substituted methine group, wherein at least two of which represent said methine group; X represents methine; Y represents an optionally substituted imino or oxygen atom. These novel spiro compounds exhibit neuropeptide Y receptor (NPY) antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders, central nervous system disorders, metobolic diseases and the like.
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Page column 55
(2010/01/21)
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- Phthalazine derivatives phosphodiesterase 4 inhibitors
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The present invention provides a compound selected from the group including: 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-phenyl-phthalazine; 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-carboxylic acid methyl ester; benzyl-{3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-ynyl}-methyl-amine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(5-morpholin-4-yl-pent-1-ynyl)-phthalazine dihydrochloride; 3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-yn-1-ol; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-morpholin-4-yl-phthalazine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-(1,2,4)triazol-1-yl-phthalazine; N→O derivatives thereof; and pharmaceutically acceptable salts thereof. The invention also provides a pharmaceutical composition which includes a therapeutically effective amount of the above compound in admixture with a suitable carrier.
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- Spiro compounds
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Spiro compounds of the general formula (I): wherein Ar1represents an optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W each represent a nitrogen atom or an optionally substituted methine group, wherein at least two of which represent said methine group; X represents nitrogen; Y represents an optionally substituted imino or oxygen atom, which exhibit neuropeptide Y receptor (NPY) antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders, central nervous system disorders, metobolic diseases and the like.
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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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- 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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- 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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- Silicon-Mediated Synthesis of Bibenzyl Systems: Synthesis of Ring and Side-Chain Functionalized Hexestrol Derivatives
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Derivatives of hexestrol , a non-steroidal estrogen, bearing photochemically reactive functional groups or γ-emmitting radionuclides, are useful as affinity labeling agents for the estrogen receptor or as imaging agents for receptor positive breast tumors, respectively.We have developed convenient synthetic routes to two side chain functionalized and aromatic ring functionalized hexestrol derivatives, based on a direct benzylic coupling reaction mediated by allylsilanes or silyl ketene acetals. 1-Dehydrohexestrol and variousaromatic ring substituted 1-dehydrohexestrol derivatives can be prepared by coupling 3-(trimethylsilyl)-1-(4-methoxyphenyl)propene with various reactive benzylic derivatives, and pentestrol derivatives are prepared by the coupling of the silyl ketene acetal derivative of p-methoxyphenyl acetic ester with benzylic derivatives.The R*,S* (erythro) and R*,R* (threo) diastereomers formed in each case can be separated readily by chromatography and recrystallization.This silicon-mediated approach to functionalized hexestrol derivatives provides a convenient route to many compounds of interest as biochemical probes and receptor-based diagnostic reagents.
- Mohan, Raju,Katzenellenbogen, John A.
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p. 1238 - 1246
(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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- 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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