873-67-6

• Article title
• Article abstract
• Author
• Journal number and time
• Download

• AOT-based microemulsions accelerate the 1,3-cycloaddition of benzonitrile oxide to N-ethylmaleimide
• We studied the 1,3-dipolar cycloaddition of benzonitrile oxide to N-ethylmaleimide in AOT/isooctane/water microemulsions at 25.0 °C and found the reaction rate to be roughly 150 and 35 times greater than that in isooctane and pure water, respectively. The
• Engberts,Fernandez,Garcia-Rio,Leis

• p. 6118 - 6123

  (2006)
• Read Online

• New approaches to the synthesis of canthin-4-one alkaloids and synthetic analogues
• Two novel approaches to the canthin-4-one ring system have been worked out. Claisen-type condensation of 1-acetyl-β-carboline with N-acyl benzotriazoles gives, via intermediate 1,3-diketones, 6-alkylcanthin-4-ones in one single operation, but this protocol is restricted to small alkyl substituents. An alternative approach, via 1-ethynyl-β-carboline and 1-isoxazolyl-β-carbolines, followed by reductive isoxazole cleavage and cyclization, is more versatile. 5,6-disubstituted canthin-4-ones are accessible via iodination at C-5 and subsequent Pd-catalyzed cross-coupling.
• Tremmel, Tim,Bracher, Franz

• p. 4640 - 4646

  (2015)
• Read Online

• Ionic liquids: Just molten salts after all?
• While there has been much effort in recent years to characterise ionic liquids in terms of parameters that are well described for molecular solvents, using these to explain reaction outcomes remains problematic. Herein we propose that many reaction outcom
• Yau, Hon Man,Chan, Si Jia,George, Stephen R. D.,Hook, James M.,Croft, Anna K.,Harper, Jason B.

• p. 2521 - 2534

  (2009)
• Read Online

• Pseudo-Interphase of Liposome Promotes 1,3-Dipolar Cycloaddition Reaction of Benzonitrile Oxide and N -Ethylmaleimide in Aqueous Solution
• The hydrophobic interior of a liposome membrane was used as a platform for the organic synthesis of hydrophobic compounds in water. The 1,3-dipolar cycloaddition of benzonitrile oxide (BNO) and N-ethylmaleimide (EMI) in liposome suspensions was carried ou
• Iwasaki, Fumihiko,Suga, Keishi,Umakoshi, Hiroshi

• p. 9772 - 9779

  (2015)
• Read Online

• Synthesis of 2-(12-aryldodecanoyl)cyclohexane-1,3-diones
• Synthesis was developed of 2-(10-undecenoyl)cyclohexane-1,3-diones containing in the side chain keto and hydroxy groups and a phenyl substituent. The synthesis is underlain by a nitrile oxide approach. The scheme included isoxazole synthesis for the prote
• Vasilyeva

• p. 1637 - 1641

  (2017)
• Read Online

• Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors
• α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.
• Umm-E-Farwa,Ullah, Saeed,Khan, Maria Aqeel,Zafar, Humaira,Atia-tul-Wahab,Younus, Munisaa,Choudhary, M. Iqbal,Basha, Fatima Z.

• (2021/05/10)
• 

• One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies
• Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.
• Karthik, B.,Kumar, A. Kannan,Nukala, Satheesh Kumar,Ravinder, M.,Swamy, T. Narasimha

• p. 1269 - 1275

  (2021/12/23)
• 

• Regioselective [3+2] cycloaddition of nitrile oxides to 1Н-pyrrole-2,3-diones: synthesis of spiro[pyrroledioxazoles]
• [Figure not available: see fulltext.] 1,3-Dipolar cycloaddition of 1H-pyrrole-2,3-diones to nitrile oxides generated in situ from N-hydroxybenzimidoyl chlorides by the action of triethylamine proceeds regioselectively with the formation of 1,4,2-dioxazole
• Moroz, Anna А.,Dmitriev, Maksim V.,Maslivets, Andrey N.

• p. 1230 - 1234

  (2022/01/31)
• 

• Reactions of 1,2,4-Oxadiazole[4,5-a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4-Oxadiazoles
• 1,2,4-Oxadiazole[4,5-a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4-oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4-oxadiazoles when treated with suitable nucleophiles or, alternatively, to give pyridones in the presence of bicarbonate. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole derivatives. The mechanism is also discussed in the light of previous observations.
• Moiola, Mattia,Leusciatti, Marco,Quadrelli, Paolo

• p. 195 - 199

  (2020/03/06)
• 

• Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions
• Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.
• Antonietti, Markus,Guldi, Dirk M.,Hussain, Tanveer,Karton, Amir,Markushyna, Yevheniia,Mazzanti, Stefano,Oschatz, Martin,Sánchez Vadillo, José Manuel,Savateev, Aleksandr,Strauss, Volker,Tarakina, Nadezda V.,Tyutyunnik, Alexander P.,Walczak, Ralf,ten Brummelhuis, Katharina

• p. 15061 - 15068

  (2020/06/17)
• 

• One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols
• A simple and efficient, one-pot approach for the synthesis of ether-linked diisoxazole derivatives has been developed through sequential reactions, which includes O-propargylation of 2-bromohomoallylic alcohols with propargyl bromide in the presence of so
• Zhang, Xiao-Lan,Wei, Mei-Hong,Chen, Jun-Min,Liu, Xiao-Ling

• p. 97 - 103

  (2019/11/16)
• 

• 1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives
• New phosphonate-containing five-membered heterocyclic dioxazole derivatives are synthesized via 1,3-dipolar cycloaddition reactions of nitrile oxides used as dipole with acyl phosphonates under basic conditions. Herein, acyl phosphonates take part in the
• Polat-Cakir, Sidika

• p. 461 - 467

  (2020/12/09)
• 

• Cycloaddition Strategies for the Synthesis of Diverse Heterocyclic Spirocycles for Fragment-Based Drug Discovery
• In recent years the pharmaceutical industry has benefited from the advances made in fragment-based drug discovery (FBDD) with more than 30 fragment-derived drugs currently marketed or progressing through clinical trials. The success of fragment-based drug
• King, Thomas A.,Stewart, Hannah L.,Mortensen, Kim T.,North, Andrew J. P.,Sore, Hannah F.,Spring, David R.

• p. 5219 - 5229

  (2019/08/12)
• 

• Cu(I)-Catalysis of One-Pot Synthesis of Some Novel Regioselective Isoxazole-Benzimidazole Hybrids and Their In Vitro Anti-Cancer Evaluation
• Regioselective synthesis of some novel isoxazole-benzimidazole hybrids in high yields via Cu(I)-catalyzed tandem one-pot reaction of aromatic aldehydes with 1-prop-2-ynylbenzimidazole is developed. Structures of the synthesized compounds are confirmed by
• Ashok Kumar,Shanmukha Kumar Jagarlapudib

• p. 2512 - 2515

  (2020/02/25)
• 

• Synthesis of 3,5-Disubstituted Isoxazoles through a 1,3-Dipolar Cycloaddition Reaction between Alkynes and Nitrile Oxides Generated from O-Silylated Hydroxamic Acids
• In this paper, we report the regioselective synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition between alkynyl dipolarophiles and nitrile oxide dipoles generated in-situ from O-silylated hydroxamic acids in the presence of trifluoromethanesulfonic anhydride and NEt3. Thanks to the mild, metal-free and oxidant-free conditions that this strategy offers, the reaction was successfully applied to a wide variety of alkynyl dipolarophiles, demonstrating the tolerance of this approach to diverse functional groups. In particular, we have shown that the method was compatible with biological molecules such as peptides and peptide nucleic acids (PNA). This protocol constitutes another example of metal-free 1,3-dipolar cycloaddition leading to the regioselective formation of isoxazoles.
• Carloni, Laure-Elie,Mohnani, Stefan,Bonifazi, Davide

• p. 7322 - 7334

  (2019/11/05)
• 

• Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles
• Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.
• Lohrer, Bernhard,Bracher, Franz
• supporting information

  (2019/11/26)
• 

• Pd/Mn Bimetallic Relay Catalysis for Aerobic Aldoxime Dehydration to Nitriles
• A Pd/Mn bimetal system was found to be an effective catalyst for dehydration of aldoximes to the useful nitriles under mild aerobic conditions. Different to the known metal-catalyzed aldoxime dehydration reactions, this reaction very possibly proceeded via an alternative mechanism of Pd/Mn bimetal relay catalysis involving a Mn-catalyzed aerobic oxidation of aldoximes to nitrile oxides by air and a Pd-catalyzed oxygen transfer from the nitrile oxides to the solvent acetonitrile. This method tolerates a variety of substrates including sterically bulky ones and also the natural product derivative. (Figure presented.).
• Zhang, Dongliang,Huang, Yaping,Zhang, Erlei,Yi, Rong,Chen, Chao,Yu, Lei,Xu, Qing
• supporting information

  p. 784 - 790

  (2018/01/04)
• 

• An efficient protocol for the synthesis of six-membered N, O-heterocycles via a 1,3-dipolar (3+3) cycloaddition between nitrile oxide and α-diazo esters
• In this manuscript, we are reporting an efficient protocol for the construction of highly functionalized N, O-heterocyclic derivatives such as 1,2,4-oxadiazine and 1,4,2-dioxazine-6-carboxylate derivatives via a 1,3-dipolar (3 + 3) cycloaddition between nitrile oxide and unprotected α-diazo esters in the presence of 2 mol% Cu(OTf)2 catalyst. The expected N, O-heterocycles were obtained in excellent yields. These N, O-heterocycles are known to exhibit insecticidal and acaricidal properties.
• Kuruba, Bharath Kumar,Vasanthkumar, Samuel

• p. 3860 - 3865

  (2017/06/14)
• 

• Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin
• A series of novel enantiomerically pure spiro-isoxazolidines and spiro-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition using respectively two dipoles, nitrones and nitrile oxides, on the exocyclic double bond of the B ring of t
• Zaki, Mohamed,Oukhrib, Abdelouahd,Akssira, Mohamed,Berteina-Raboin, Sabine

• p. 6523 - 6529

  (2017/02/05)
• 

• Design, Synthesis, and Conformational Analysis of Proposed β-Turn Mimics from Isoxazoline-Cyclopentane Aminols
• Constrained aminols from oxazanorbornene derivatives have the geometrical features to be used as β-turn inducers. Four different stereoisomers were prepared and spectroscopically characterized (MD calculations, NMR-titration and VT-NMR experiments). Temperature coefficients in DMSO are indicative for the existence of an intramolecular hydrogen bond. Chirooptical properties revealed a β-turn arrangement of all the synthesized compounds, where, depending on the absolute configuration of the cyclopentane spacer, they can be labeled as left- or right-handed turns.
• Memeo, Misal Giuseppe,Mella, Mariella,Montagna, Valentina,Quadrelli, Paolo

• p. 16374 - 16378

  (2015/11/09)
• 

• Radioiodinated fatty acids
• The present invention provides novel radioiodinated fatty acids. Also provided are methods of preparation of said radioiodinated fatty acids from non-radioactive precursors, as well as radiopharmaceutical compositions comprising such radioiodinated fatty acids. The invention also provides in vivo imaging methods using the radioiodinated fatty acids.
• -
• Page/Page column 16; 17

  (2015/11/16)
• 

• Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas disease
• Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5-dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g) was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to 1 μM). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.
• Rodrigues, Giseli Capaci,Feijó, Daniel Ferreira,Bozza, Marcelo Torres,Pan, Peiwen,Vullo, Daniela,Parkkila, Seppo,Supuran, Claudiu T.,Capasso, Clemente,Aguiar, Alcino Palermo,Vermelho, Alane Beatriz

• p. 298 - 308

  (2014/02/14)
• 

• Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes
• A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi
• Xiang, Changbin,Li, Tingting,Yan, Jie
• supporting information

  p. 682 - 688

  (2014/01/17)
• 

• 1,3-dipolar cycloaddition reaction of nitrile oxides revisited - Unusual side products characterized by 2d NMR
• Cycloaddition of (4-trifluoromethyl)phenylnitrile oxide to N-(4-methoxyphenyl)acrylamide afforded bicyclic tetrahydro-oxazolo-(3,2-b)[1,3] oxazine-2-carboxamide derivative in result of N-acylation of the initially formed cycloadduct by the dipolarophile.
• Gucma,Golebiewski

• p. 572 - 578

  (2014/06/10)
• 

• One-pot synthesis of isoxazolines from aldehydes catalyzed by iodobenzene
• A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.
• Han, Liuquan,Zhang, Bijun,Xiang, Changbin,Yan, Jie

• p. 503 - 509

  (2014/03/21)
• 

• Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile and its reaction with substituted nitrile N-oxides
• A procedure of synthesis of 2-(2-methyltetrazol-5-yl)-2,2- dinitroacetonitrile has been developed and its reaction with substituted nitrile N-oxides has been investigated, proceeding by the mechanism of 1,3-dipolar cycloaddition and affording 2-methyl-5-[(1,2,4-oxadiazol-5-yl)(dinitro)methyl]- 2H-tetrazoles. The latter react with KOH in ethanol forming the potassium salt of 2-methyltetrazol-5-yldinitromethane and substituted 5-hydroxy-1,2,4- oxadiazoles.
• Abdelrakhim,Tyrkov,Yurtaeva

• p. 280 - 284

  (2014/04/17)
• 

• Reaction of polyfluorinated cyclohexa-2,4-dienones with aryl nitrile oxides
• Reaction of 1,3-dipolar cycloaddition of 6-chloropentafluorocyclohexa-2,4- dienone, 6-chloro-3-(pentafluorophenoxy)tetrafluorocyclohexa-2,4-dienone, and perfluoro-6-phenoxycyclohexa-2,4-dienone with aryl nitrile oxides proceeds highly stereoselectively at
• Kovtonyuk,Gatilov, Yu. V.

• p. 1215 - 1220

  (2013/10/01)
• 

• Regio-and stereoselective synthesis of pyrrolo or azepine-fused cyclopenta[ d ]isoxazolines from 2- p -tolylsulfinylcyclopent-2-en-1-one
• Reactions of enantiopure 2-p-tolylsulfinylcyclopent-2-en-1-one with cyclic nitrones afforded pyrrolo or azepine-fused cyclopenta[d]isoxazolidines in high yields under mild conditions. Comparison of these results with those obtained with cyclopent-2-en-1-one as the dipolarophile shows that the sulfinyl group increases the reactivity of the enonic system and efficiently controls the π-facial and endo/exo selectivities of the cycloadditions, which are also dependent on the easy cycloreversion of the resulting compounds. Results obtained in reactions with other dipoles (benzonitrile oxides and those resulting from allenoate and PPh3) are also reported. 2013 Copyright Taylor and Francis Group, LLC.
• Garcia Ruano, Jose L.,Soriano, Jose F.,Fraile, Alberto,Martin, M. Rosario,Nunez, Alberto

• p. 17 - 32

  (2013/08/24)
• 

• Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
• Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
• Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
• experimental part

  p. 765 - 781

  (2011/04/15)
• 

• Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents
• Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (α-methylene- γ-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of α,β-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described.
• Reddy, Doma Mahendhar,Qazi, Naveed A.,Sawant, Sanghpal D.,Bandey, Abid H.,Srinivas, Jada,Shankar, Mannepalli,Singh, Shashank K.,Verma, Monika,Chashoo, Gousia,Saxena, Arpita,Mondhe, Dilip,Saxena, Ajit K.,Sethi,Taneja, Subhash C.,Qazi, Gulam N.,Sampath Kumar
• body text

  p. 3210 - 3217

  (2011/07/31)
• 

• Photogeneration and reactivity of acyl nitroso compounds
• Acyl nitroso compounds have been generated by photolysis of several different classes of precursors including 9,10-dimethylanthracene adducts, nitrodiazo compounds, and 1,2,4-oxadiazole-4-oxides. Consideration of the nitronate-like resonance structure of nitrodiazo compounds led to an examination of the photochemistry of nitronates with -leaving groups. Photolysis of such nitronates has been shown to generate an acyl nitroso species along with a carbene intermediate. Nanosecond time-resolved infrared (TRIR) spectroscopy has been used to detect photogenerated acyl nitroso compounds directly and to examine their reaction kinetics with amines and thiols. The mechanism of acyl nitroso aminolysis by primary amines involves general base catalysis, while the mechanism of aminolysis by secondary amines is strictly bimolecular. Thiols do not seem to be reactive with acyl nitroso compounds on the microsecond time scale, but thiolates are quite reactive. The reaction between benzoyl nitroside and an organic-soluble thiolate, tetrabutylammonium dodecanethiolate, proceeds via a proposed tetrahedral intermediate, which is observable by TRIR spectroscopy.
• Evans, Anthony S.,Cohen, Andrew D.,Gurard-Levin, Zachary A.,Kebede, Naod,Celius, Tevye C.,Miceli, Alexander P.,Toscano, John P.
• experimental part

  p. 130 - 138

  (2011/04/23)
• 

• 1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with nitrile oxides and nitrones
• 1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with nitrile oxides and nitrones is described. A?series of novel isoxazolines are isolated from the nitrile oxide cycloadditions, whilst the isoxazolines generated from the nitrone cycloadditions undergo further ring opening to yield piperidines.
• Kissane, Marie,Lawrence, Simon E.,Maguire, Anita R.
• supporting information; experimental part

  p. 4564 - 4572

  (2010/07/05)
• 

• Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids
• Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.
• Zheng, Hongchao,McDonald, Robert,Hall, Dennis G.
• experimental part

  p. 5454 - 5460

  (2010/09/15)
• 

• A novel synthesis of N-unsubstituted β-enamino thioesters from 3-arylisoxazoles and 3-aryl-5-phenylthio-2-isoxazolines
• A novel procedure for the synthesis of N-unsubstituted β-enamino thioesters, (Z)-S-phenyl 3-amino-3-arylprop-2-enethioates, from 3-arylisoxazoles or 3-aryl-5-phenylthio-2-isoxazolines is described and a plausible mechanism for the reaction is proposed. Some examples of conversion of one β-enamino thioester [(Z)-S-phenyl 3-amino-3-phenylprop-2-enethioate] into N-unsubstituted β-enaminoacyl derivatives (β-enamino esters, β-enamino amides, and β-keto amides) are also reported. Georg Thieme Verlag Stuttgart - New York.
• Vitale, Paola,Di Nunno, Leonardo,Scilimati, Antonio
• experimental part

  p. 3195 - 3203

  (2010/10/21)
• 

• Flash vacuum pyrolysis of 1,2,5-oxadiazole 2-oxides and 1,2,3-triazole 1-oxides
• The flash vacuum pyrolysis (FVP, 450-600 °C/10-3 mmHg) of 3,4-diaryl- and 3,4-dialkyl-1,2,5-oxadiazole 2-oxides (furoxans) has been investigated. In all cases the 1,2,5-oxadiazole ring cleaved cleanly at O(1)-N(2) and C(3)-C(4) to afford two nitrile oxide fragments, which were trapped in high yield (75-97%) as their isoxazoline cycloadducts by reaction with alk-1-enes. At higher temperatures (700-800 °C) isocyanates were formed as by-products. The dimerisation of acetonitrile oxide to dimethylfuroxan was followed by 1H NMR spectroscopy, and the rate constant for the 2 nd order reaction determined. The furoxans were converted into isocyanates in good yield (61-95%) by FVP, followed by sulfur dioxide-mediated isomerisation of the resulting nitrile oxides. 2,4,5-Trisubstituted-1,2,3- triazole 1-oxides showed greater thermal stability, but at 700-800 °C decomposition of the 4,5-dimethyl compound 25b lead to 1,2-di(5-methyl-2-phenyl- 1,2,3-triazol-2-yl)ethane as the major product; attempts to trap acetonitrile oxide were unsuccessful. ARKAT USA, Inc.
• Mitchell, William R.,Paton, R. Michael
• experimental part

  p. 34 - 54

  (2011/02/21)
• 

• π-face-selective 1,3-dipolar cycloadditions of 3,4-Di-tert- butylthiophene 1-oxide with 1,3-dipoles
• 3,4-Di-tert-butylthiophene 1-oxide underwent 1,3-dipolar cycloadditions with 1,3-dipoles such as nitrile oxide, diazomethane, nitrile imide, nitrone, and azomethine ylide at its syn-π-face with respect to the S=O bond. Taylor & Francis Group, LLC.
• Nakayama, Juzo,Furuya, Tomohiro,Suzuki, Yasuko,Hiraiwa, Suguru,Sugihara, Yoshiaki
• body text

  p. 1175 - 1183

  (2010/03/25)
• 

• Reactivity of arylnitrile oxides and C-aroyl-N-phenylnitrones with 3-methylenedihydro-(3H)-furan-2-one and itaconic anhydride
• 1,3-dipolar cycloaddition is a powerful route for the synthesis of five-membered heterocycles. The [3+2] cycloadditions of some α-methylene-γ-buryrolactones, namely 3-methylenedihydro-(3H)-furan-2-one (1) and itaconic anhydride (2) were studied. Their rea
• Roussel, Christophe,Ciamala, Kabula,Vebrel, Jo?l,Riche, Claude

• p. 1977 - 1991

  (2016/10/24)
• 

• From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions
• A rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed through the Grieco cycloaddition of cyclopentadiene to iminium salts. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target amin
• Quadrelli, Paolo,Piccanello, Andrea,Mella, Mariella,Corsaro, Antonino,Pistarà, Venerando

• p. 3541 - 3547

  (2008/09/21)
• 

• Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
• 3-Arylisoxazoles react with LDA in THF at 0 °C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A?fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA.
• Di Nunno, Leonardo,Vitale, Paola,Scilimati, Antonio
• experimental part

  p. 11198 - 11204

  (2009/04/11)
• 

• Anionic domino C-O-heterocyclization approach for the synthesis of 5-vinyl isoxazolines
• 5-Vinyl isoxazolines were isolated in high yields through domino nucleophilic addition-anionic C-O-heterocyclization, when allyl organometallics derived from trans-1,4-dihalobutene were reacted with nitrile oxides. Georg Thieme Verlag Stuttgart.
• Qazi, Naveed Ahmed,Singh, Parvinder Pal,Jan, Sumira,Kumar, H. M. Sampath

• p. 1449 - 1451

  (2008/02/13)
• 

• Regioselectivity in the 1,3-dipolar cycloaddition reactions of nitrile oxides and organic azides with bromocarbazole-1,4-diones
• The effect exerted by the presence of a bromine atom in 2 or 3 position of a carbazole-1,4-dione on the regiocontrol of 1,3-dipolar cycloaddition reactions with nitrile oxides and organic azides was investigated. Comparison with the results obtained with
• Compain-Batissou, Muriel,Gentili, Jacques,Walchshofer, Nadia,Domard, Monique,Fenet, Bernard,Bouaziz, Zouhair

• p. 27 - 38

  (2008/02/02)
• 

• Reaction of allenylmagnesium and allenylindium bromides with nitrile oxides: synthesis of novel 5-butynyl- and 5-methylisoxazoles
• 5-Butynylisoxazoles were obtained in high yields through a domino addition, C-O heterocyclization involving allenylmagnesium bromide and benzonitrile oxide in dry THF, in which the corresponding 5-methylisoxazoles were isolated in trace amounts. However, when the reactions were attempted in aqueous media using allenylindium bromide, 5-methylisoxazoles were formed as the sole products in high yields.
• Sampath Kumar,Singh, Parvinder Pal,Shafi, Syed,Reddy, Pitta Bhaskar,Shravankumar, Kankala,Reddy, Doma Mahender

• p. 887 - 890

  (2007/10/03)
• 

• Synthesis and molecular structure of 4-nitro-9-phenyl-1H-and 9-hydroxy-3-oxo-9-phenyl-2,3-dihydro-9H-indeno-[2,1-c]pyridines and 3,7-diphenyl-3a, 4,5,6-tetrahydroindeno[2,1-c]isoxazolo[5,4-d]pyridine
• The 4-nitro derivatives and an oxidation by-product, 9-hydroxy-2-methyl-3- oxo-9-phenyl-2,3-dihydro-9H-indeno[2,1-c]pyridine were obtained by the nitration of N-alkyl-9-phenyl-2,3-dihydro-1H-indeno-[2,1-c]pyridines with sodium nitrite in acetic acid. Thei
• Volkov,Levov,Soldatenkov,Kolyadina,Volkova,Khrustalev

• p. 1181 - 1188

  (2008/09/19)
• 

• Stereoselective dimerization of 3-arylisoxazoles to cage-shaped bis-β-lactams syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by hindered lithium amides
• 3-Arylisoxazoles react with hindered lithium amides giving syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones in good to fair yields. Stereochemistry of the so-obtained cage-shaped bis-β-lactams was assigned by X-ray diffraction analysis. Concerning the mechanism of formation of such hitherto unknown molecules, dimerization of an azetinone anion intermediate stereoselectively induced by Li+ chelation is suggested.
• Di Nunno, Leonardo,Vitale, Paola,Scilimati, Antonio,Simone, Laura,Capitelli, Francesco

• p. 12388 - 12395

  (2008/03/13)
• 

• One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles
• 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional
• Hansen, Trond V.,Wu, Peng,Fokin, Valery V.

• p. 7761 - 7764

  (2007/10/03)
• 

• Method for preparing 3,4-diphenyl-substituted isoxazole compounds
• The present invention relates to a process for preparing diaryl-substituted isoxazole using compounds of Formula (V) and Formula (VII): where Y is and to processes for preparing valdecoxib and parecoxib.
• -
• Page/Page column 8

  (2008/06/13)
• 

• One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide
• Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.
• Sheng, Shou-Ri,Liu, Xiao-Ling,Xu, Qu,Song, Cai-Sheng

• p. 2763 - 2764

  (2007/10/03)
• 

• A novel synthesis of isoxazoles via 1,3-dipolar cycloaddition of nitrile oxides to acetyl acetone
• Nitrile oxides (2) isolated from the oxidative dehydrogenation of aldoximes (1) by chloramines-T react with acetyl acetone (3) to afford 4-acetyl-3-aryl-5-methyl isoxazoles (5) in good yield. All new compounds were characterized by IR, 1H NMR,
• Umesha,Kumar, K. Ajay,Rai, K. M. Lokanatha

• p. 1841 - 1846

  (2007/10/03)
• 

• Design and Synthesis of a Piperazinylalkylisoxazole Library for Subtype Selective Dopamine Receptor Ligands
• A piperazinylbutylisoxazole library was designed, synthesized and screened for the binding affinities to dopamine D2, D3, and D4 receptors. Several ligands were identified to possess high binding affinity and selectivity for the D3 and D4 receptors over the D2 receptor. Compounds 6s and 6t showed Ki values of 2.6 nM and 3.9 nM for the D3 receptor with 46- and 50-fold selectivity over te D2 receptor, respectively.
• Cha, Mi Young,Choi, Byung Chul,Kang, Kyung Ho,Pae, Ae Nim,Choi, Kung Il,Cho, Yong Seo,Koh, Hun Yeong,Lee, Hee-Yon,Jung, Daeyoung,Kong, Jae Yang

• p. 1327 - 1330

  (2007/10/03)
• 

• Sugar-based ethenyl ethers: Stereoselective dipolar cycloadditions of nitrile oxides
• Selected sugar-based ethenyl ethers have been employed in 1,3-dipolar cycloaddition with nitrile oxides. In the D-fructo series, high diastereoselectivity was observed as compared with the 3-epimeric D-psico series.
• Desroses, Matthieu,Chery, Florence,Tatibouet, Arnaud,De Lucchi, Ottorino,Rollin, Patrick

• p. 2535 - 2539

  (2007/10/03)
•