- Oxidized Phenyl-Substituted Sesquibicyclic Hydrazines
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The effect of α- and β-phenyl substituents on the neutral, +1, and +2 oxidation states of bis-N,N'-bicyclic hydrazines 1 and 2 is discussed.An α-phenyl substituent on 2 makes first electron removal 1.8 kcal/mol more difficult, but second electron removal
- Nelsen, Stephen F.,Wang, Yichun,Hiyashi, Randy K.,Powell, Douglas R.,Neugebauer, Franz A.
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- Silica-supported ICI as a novel heterogeneous system for the rapid oxidation of urazoles to triazolinediones
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ICl-SiO2 as a new reactive system was prepared by the treatment of iodine monochloride with an activated silica gel in chloroform. ICl-SiO 2 in a heterogeneous system efficiently oxidized urazoles to the corresponding triazolinediones under mild conditions in high yields at room temperature.
- Karami, Bahador,Mallakpour, Shadpour,Farahi, Mahnaz
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- Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di- And Triurazole Radicals
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Dynamic covalent chemistry (DCvC) describes systems in which readily reversible bond formation allows for control of product distributions by straightforward manipulation of reaction conditions (e.g., changes in temperature, solvent, concentration, etc).
- Breton, Gary W.,Martin, Kenneth L.
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- Chemoenzymatic synthesis of enantiopure 1-azafagomine
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A new chemoenzymatic synthesis of both enantiomeric forms of the glycosidase inhibitor 1-azafagomine (1) is reported. The synthesis starts from the achiral starting materials pentadienol and methylurazol with the key steps being a hetero-Diels-Alder reaction followed by a lipase R/Novozym 435- catalyzed enantioselective esterification of the Diels-Alder adduct.
- Liang, Xifu,Bols, Mikael
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- Silica chloride/NaNO2 as a novel heterogeneous system for the oxidation of urazoles under mild conditions
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Urazoles and bis-urazoles can be converted in excellent yields to their corresponding triazolinediones, with a combination of silica chloride (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature.
- Zolfigol, Mohammad Ali,Torabi, Mehdi,Mallakpour, Shadpour E
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- Development of a Scalable and Sublimation-Free Route to MTAD
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The cyclic azodicarbonyl 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) is a versatile and powerful reagent used mainly in cycloaddition chemistry. Though known for more than 50 years, its unsafe preparation, as well as purification by sublimation, hampered i
- Siddiqi, Zohaib R.,Ungarean, Chad N.,Bingham, Tanner W.,Sarlah, David
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- Diels-Alder Reactions of Protoporphyrin IX Dimethyl Ester
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The reaction of a divinyl porphyrin (protoporphyrin IX dimethyl ester) with a number of azo dienophiles was studied.In all cases where reaction occurred and the product could be isolated, the expected addition product was observed.In most cases, / adducts were also identified.
- Morgan, Alan R.,Kohli, Dilmeet H.
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- An efficient method for the oxidation of urazoles with [NO+·crown· H(NO3)2-]
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An ionic complex has been obtained from N2O4 in the presence of the macrocyclic polyether 18-crown-6. This crystalline compound was used as an effective oxidizing agent for the oxidation of urazoles to their corresponding triazolinediones at room temperature with excellent yields.
- Zolfigol, Mohammad Ali,Zebarjadian, Mohammad Hassan,Chehardoli, Gholamabbas,Mallakpour, Shadpour E,Shamsipur, Mojtaba
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- Oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions via in situ generation of NO+IOx-
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A combination of periodic or iodic acids and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with good yields.
- Zolfigol,Chehardoli,Shirini,Mallakpour,Nasr-Isfahani
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- A convenient method for the oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with sodium nitrate and oxalic dihydrate
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A combination of oxalic acid dihydrate and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bisurazoles to their corresponding triazolinediones at room temperature with good yields.
- Zolfigol, Mohammad Ali,Mallakpour, Shadpour E.
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- An efficient method for the oxidation of urazoles under mild and heterogeneous conditions
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A combination of inorganic acidic salts or silica gel-supported inorganic acids and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogenous conditions in good yields. Silica gel supported nitric acid and ceric ammonium nitrate (CAN) are also capable of effecting these oxidations in the absence of sodium nitrite in moderate to good yields. Mg(HSO4)2 is a superior to all the aforementioned reagents in convenience, yield and purity of the isolated triazolinediones.
- Zolfigol, Mohammad Ali,Borazjani, Maryam Kiany,Mallakpour, Shadpour E.,Nasr-Isfahani, Hossein
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- 1,4-Diazabicyclo[2.2.2]octane 1,4-bis(oxide)-bis(hydrogen peroxide)/MClx as a novel heterogeneous system for the oxidation of urazoles under mild conditions
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A combination of inorganic hydrolyzable chloride salts and 1,4-diazabicyclo[2.2.2]octane 1,4-bis(oxide)-bis(hydrogen peroxide), DABCO-DNODP, in the presence of wet SiO2 is used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with good to excellent yields.
- Zolfigol, Mohammad Ali,Salehi, Peyman,Mallakpour, Shadpour E.,Torabi, Mehdi
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- Oxidation of urazoles under mild and heterogeneous conditions with KHSO5 and NaNO2
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A combination of potassium monopersulfate and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with excellent yields.
- Zolfigol,Bagherzadeh,Chehardoli,Mallakpour
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- Effects of CNN Bond Angle Restriction in 2,3-Diazabicyclohexane Derivatives on Nitrogen Inversion Barrier, Ease of Oxidation, and Acidity
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Restriction of the CNN angle of triazolidinedione 3 by the presence of the diazabicyclohexyl system causes the nitrogens to be more pyramidal than tetrahedral (α(av) for crystalline 3 is 109.2 deg) and produces a double nitrogen inversion barrier o
- Nelsen, Stephen F.,Petillo, Peter A.,Chang, Hao,Frigo, Timothy B.,Dougherty, Dennis A.,Kaftory, Menahem
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- Photolysis of matrix-isolated 4-R-1,2,4-triazoline-3,5-diones: Identification of aziridine-2,3-dione transients
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Matrix-isolated 4-methyl-1,2,4-triazolinedione la and 4-phenyl-1,2,4-triazolinedione 1b were photolyzed at λ335 nm and λ≥310 nm, respectively. The reactions induced by photolysis were monitored by FT-IR spectroscopy. The isocyanates 2a and 2b are always the more abundant products with carbon monoxide. Methyl- and phenylaziridine-2,3-diones (3a and 3b) were detected as minor, but well-identified reaction products. The IR experimental absorption bands were assigned by comparison with literature data and with simulated infrared spectra obtained by ab initio calculation at the 6-31G* level. Stable at the matrix temperature (10 K), 3a and 3b photolyzed to isocyanates and CO when irradiated at λ≥230 nm. Irradiation of 2b at this wavelength induces its decomposition. The kinetic data show that the rate constant process 1a→2a is faster than the 1a→3a process (3.29×10-3 and 2.35×10-4 min-1 respectively).
- Risi, Florence,Pizzala, Louis,Carles, Micheline,Verlaque, Patrick,Aycard, Jean-Pierre
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- Preparation of 2-(alkylcarbamoyl)hydrazine-1-carboxylic acid alkyl ester or its corresponding urazole salt
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The present invention relates to the preparation of 2-(alkylcarbamoyl)hydrazine-1-carboxylic acid alkyl ester or its corresponding urazole salt. The present invention relates to 2-(alkylcarbamoyl)hydrazine-1-alkyl carboxylate or its corresponding derivative alkyl-4H-1,2,4-triazole-3,5-diol salt (urine Azole salt) preparation. This is particularly advantageous because it uses a one-pot reaction and uses alkyl acetate as the solvent in steps a) and b) of its synthesis.
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Paragraph 0155-0157
(2021/06/23)
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- METHOD FOR PRODUCING SOLID TRIAZOLINEDIONE COMPOUND, SOLID TRIAZOLINEDIONE COMPOUND, AND METHOD FOR PRODUCING TRIAZOLINEDIONE COMPOUND
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Provided are a method for separating a DAPTAD-containing triazolinedione compound in solid form from a reaction solution, a separated solid triazolinedione compound, and a novel method for producing a triazolinedione compound. A triazolinedione solution in which a DAPTAD-containing triazolinedione compound is dissolved is brought into contact with a C5-15 hydrocarbon-based poor solvent to obtain a solid triazolinedione compound. Also, a triazolinedione compound is oxidized using an oxidizing agent that does not produce acid as a byproduct to obtain a triazolinedione compound.
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Paragraph 0164-0167
(2020/12/25)
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- TYROSINE-SPECIFIC FUNCTIONALIZED INSULIN AND INSULIN ANALOGS
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The present invention relates to tyrosine-specific functionalized insulin analogs and processes of making such tyrosine-specific functionalized insulin analogs using R-3H-1,2,4-triazoline-3,5-(4H)diones (PTAD).
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Page/Page column 40-42
(2019/10/15)
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- TYROSINE LIGATION PROCESS
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A process is provided for preparing a conjugate of Formula (I-A) or (I) comprising a polypeptide (or a protein) containing n number of tyrosine units, where n is an integer greater than or equal to 1, dispersed within the amino acid chain having an amino terminus end (A1) and an acid terminus end (A2) of the protein or polypeptide (either the amino or acid terminus end can be the at least one tyrosine unit) and having a weight average molecular weight equal to or greater than 10,000 Daltons (10 kDa), wherein the conjugate comprises a number m of tyrosine conjugates (modified tyrosine residues) as depicted in Formula (I-A) or (I), where m is at least one and is less than or equal to n: where X, Lg, L and R are as defined herein.
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Page/Page column 66
(2013/03/26)
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- Application of radical cation spin density maps toward the prediction of photochemical reactivity between N -methyl-1,2,4-triazoline-3,5-dione and substituted benzenes
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Visible light irradiation of N-methyl-1,2,4-triazoline-3,5-dione in the presence of substituted benzenes is capable of inducing substitution reactions where no reaction takes place thermally. In addition to the formation of 1-arylurazole products resultin
- Breton, Gary W.,Hoke, Kevin R.
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p. 4697 - 4707
(2013/06/27)
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- N2O4 chemisorbed onto n-propylsilica kryptofix 21 and kriptofix 22 as two new functional polymers for the fast oxidation of urazoles and 1,4-dihydropyridines
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3-Chloropropylsilica was reacted with Kriptofix 21 or 22 in the presence of triethylamine to form N-propylsilica Kryptofix 21 and Kriptofix 22. Then N 2O4 was added to each of these polymers to chemisorb onto cavity of aza-crown ethers. These functionalized polymers were applied for the fast and simple oxidation of urazoles and 1,4-dihydropyridines, respectively.
- Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Ghaemi, Ezat,Madrakian, Elaheh,Niknam, Khodabakhsh,Mallakpour, Shadpour
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experimental part
p. 596 - 599
(2012/09/07)
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- Oxidation of urazoles to their corresponding triazolinediones using benzyltriphenylphosphonium nitrate
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Benzyltriphenylphosphonium nitrate in the presence of AlCl3 oxidised 1,2,4-triazolidine-3,5-diones to the corresponding 4-substituted-1,2,4- triazole-3,5-diones.
- Samimi, Heshmat Allah,Parvanak, Kaveh
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experimental part
p. 272 - 274
(2011/10/07)
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- Iodogen: A novel reagent for the oxidation of urazoles under heterogeneous conditions
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Iodogen is employed as an efficient oxidizing agent for the conversion of urazoles and bis-urazoles into the corresponding 1,2,4-triazoles in good to excellent yields under mild heterogeneous conditions at room temperature. Georg Thieme Verlag Stuttgart.
- Khoramabadi-Zad, Ahmad,Shiri, Azam,Zolfigol, Mohammad Ali,Mallakpour, Shadpour
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scheme or table
p. 2729 - 2732
(2010/01/21)
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- PEG-N2O4 system as an efficient reagent both for the rapid oxidation of urazoles and 1,4-dihydropyridines under nonaqueous conditions
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N2O4 was easily impregnated on polyethyleneglycol to give a stable reagent. Polyethyleneglycol-N2O4 (PEG-N 2O4) system was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones and also for the aromatization of 1,4-dihydropyridines into the corresponding pyridine derivatives under mild conditions at room temperature with good to excellent yields.
- Zolfigol, Mohammad Ali,Ghaemi, Ezat,Madrakian, Elaheh,Niknam, Khodabakhsh
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experimental part
p. 704 - 711
(2009/05/26)
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- N-bromo reagent mediated oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions
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Various N-bromo reagents [HMTAB, DABCO-bromine, DPTBE, and TBCA] were used as effective oxidizing agents for the oxidation of urazoles and bisurazoles to their corresponding triazolinediones under mild and heterogeneous conditions at room temperature with good to excellent yields. Also the oxidation of some new 4-phenylurazole derivatives with these reagents is discussed.
- Zolfigol, Mohammad Ali,Chehardoli, Gholamabbas,Ghaemi, Ezat,Madrakian, Elaheh,Zare, Reza,Azadbakht, Tahereh,Niknam, Khodabakhsh,Mallakpour, Shadpour
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experimental part
p. 261 - 265
(2009/05/26)
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- Oxidation of urazoles with 1,3-dihalo-5,5-dimethylhydantoin, both in solution and under solvent-free conditions
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1,3-dichloro-5,5-dimethylhydantoin (DCH) and 1,3-dibromo-5,5- dimethylhydantoin (DBH) were used as effective oxidizing agents for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild conditions at room temperature with good to excellent yields.
- Zolfigol, Mohammad Ali,Nasr-Isfahani, Hossein,Mallakpour, Shadpour,Safaiee, Maliheh
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p. 761 - 764
(2007/10/03)
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- Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the oxidation of urazoles under mild conditions
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Neat chlorosulfonic acid reacted with silica gel to give silica sulfuric acid (I) in which sulfuric acid functions immobilized on the surface of silica gel via covalent bonding. Urazoles and bis-urazoles can be readily converted to their corresponding triazolinediones with a combination of silica sulfuric acid (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature.
- Zolfigol, Mohammad Ali,Chehardoli, Gholamabbas,Mallakpour, Shadpour E.
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p. 833 - 841
(2007/10/03)
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- Trichloroisocyanuric acid as a novel oxidizing agent for the oxidation of urazoles under both heterogeneous and solvent free conditions
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Trichloroisocyanuric acid was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under both heterogeneous and also solvent free conditions with excellent yields at room temperature.
- Zolfigol, Mohammad Ali,Madrakian, Elaheh,Ghaemi, Ezat,Mallakpour, Shadpour
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p. 1633 - 1636
(2007/10/03)
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- Oxidation of urazoles via in situ generation of Cl+ by using N,N,2,3,4,5,6-heptachloroaniline or a UHP/MCln system under mild conditions
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A combination of inorganic hydrolysable chloride salts and UHP (hydrogen peroxide-urea complex) in the presence of wet SiO2 was used as an effective oxidising agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions in good to excellent yields. Oxidation of urazoles and bis-urazoles also occurred with N,N,2,3,4,5,6-heptachloroaniline. The in situ generation of Cl+ appears to be required for the oxidation of urazoles using these reagents.
- Zolfigol,Bagherzadeh,Chehardoli,Mallakpour,Mamaghani
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p. 390 - 393
(2007/10/03)
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- Further studies of the thermal and photochemical Diels-Alder reactions of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with naphthalene and some substituted naphthalenes
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MeTAD thermally reacted with naphthalene (2) and methylated naphthalenes to give equilibrium mixtures of starting materials and [4 + 2] cycloadducts. Methyl substitution on the naphthalene ring generally increased both the amount of cycloadduct formed and the rate of cycloaddition relative to 2. The isolated cycloadducts were all thermally labile and quantitatively reverted to the parent naphthalene in the presence of 2,3-dimethyl-2-butene as a trap for liberated MeTAD. The rates of the cycloreversion reactions were affected by substitution patterns but not appreciably by solvent. A mechanism for the cycloaddition reaction is presented that proposes the involvement of a charge-transfer complex. Photochemically, MeTAD demonstrated lower regioselectivity in its reactions with substituted naphthalenes relative to the corresponding thermal reactions.
- Breton, Gary W.,Newton, Kristy A.
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p. 2863 - 2869
(2007/10/03)
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- Oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions
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A combination of sodium hydrogen sulfate and sodium nitrite in the presence of wet SiO2 is used as an effective oxidizing agent for the oxidation of urazoles and bisurazoles to their corresponding triazolinediones at room temperature with excellent yields.
- Zolfigol,Mallakpour,Madrakian,Ghaemi
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p. 308 - 310
(2007/10/03)
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- Electrosynthesis of cyclic α-carbonylazo compounds. Chemical stability of the electrogenerated dienophiles and in situ trapping of dienes
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Dienophilic cyclic α-carbonylazo compounds were prepared electrochemically by oxidation of the corresponding hydrazino compounds using a flow cell fitted with a graphite felt anode in acidic methanol or acetonitrile. The instability of these compounds in methanol was first studied. In situ Diels-Alder additions of these electrogenerated dienophiles and various dienes were performed in relatively good yields in acidic methanol or acetonitrile.
- Lorans,Hurvois,Moinet
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p. 807 - 813
(2007/10/03)
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- Addition of N-methyltriazolinedione to biadamantylidene
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The addition of N-methyltriazolinedione (M) to biadamantylidene (A) gives the [2 + 2) adduct P, but clearly does not proceed in one step beause an aminoaziridinium intermediate (I) can be observed to build up during the reaction. The overall rate of P for
- Nelsen, Stephen F.,Klein, Susan J.
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p. 456 - 460
(2007/10/03)
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- The Reaction of Imidazopyridines with Methyl- and Phenyltriazolonediones and with Diethyl Azodicarboxylate
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Imidazopyridines react in one of two ways with methyl- and phenyl triazolinediones and diethyl azodicarboxylate to give either Michael type addition products at C-3 or C-1, or novel 1,2,4-triazolines.The nature of the product depends upon the dienophile and the substitution pattern of the imidazopyridine.
- Anderson, David J.,Watt, William
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p. 1525 - 1530
(2007/10/03)
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- AN IMPROVED SYNTHESIS OF ETHYL AZODICARBOXYLATE AND 1,2,4-TRIAZOLINE-3,5-DIONES USING HYPERVALENT IODINE OXIDATION
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Hypervalent iodine oxidation of 1,2-dicarbethoxy hydrazine (1) and 4-substituted urazoles (3) using iodobenzene diacetate or pentafluoroiodobenzene bis-trifluoroacetate in CH2Cl2 at room temperature proceeds smoothly to yield ethyl azodicarboxylate (2) and 4-substituted 1,2,4-triazoline-3,5-diones (4) in excellent yields.
- Moriarty, Robert M.,Prakash, Indra,Penmasta, Raju
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p. 409 - 414
(2007/10/02)
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- The Synthesis of 8,10,12-Triazaprostaglandin Analogues: 1,2,4-Triazolidine-3,5-dione Derivatives
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In the search for active, more selective prostaglandin analogues, the synthesis of 8,10,12-triazaprostaglandin analogues has been achieved from readily available 4-methyl-1,2,4-triazolidine-3,5-dione.The general approach involved introduction of the α- and ω-side-chain as entire units by step-wise N-alkylation.The problems encountered with this approach of competing N- and O-mono- and di-alkylation were overcome, eventually, such that judicious choice of the initial mono-N-alkylation step enabled the synthesis of analogues incorporating wide variations in the α- and ω-side-chain.Important structural modifications included introduction of unsaturation into the α-side-chain at the 5,6-position and of methyl groups into the ω-side-chain at the 15- and 16-position as exemplified by the synthesis of 1--2-(3-hydroxy-3,4-dimethyloctyl)-4-methyl-1,2,4-triazolidine-3,5-dione (19).The stable triazaprostaglandin analogues were synthesized as racemic compounds but, nevertheless, compound (19) possessed bronchodilator activity of a similar order to that of the natural prostaglandins PGE1 and PGE2.
- Adams, David R.,Barnes, Alan F.,Cassidy, Frederick,Thompson, Mervyn
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p. 2061 - 2068
(2007/10/02)
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