- BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties
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A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.
- Brar, Amandeep,Unruh, Daniel K.,Ling, Natalie,Krempner, Clemens
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supporting information
p. 6305 - 6309
(2019/08/20)
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- Selective Oxidation of Secondary Amines to N,N-Disubstituted Hydroxylamines by Choline Peroxydisulfate
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N,N-Disubstituted hydroxylamines were prepared directly from secondary amines by a reliable method using an oxidizing task-specific ionic liquid, choline peroxydisulfate. The operational simplicity, high selectivity, and green reaction conditions, make this method efficient and practical.
- Banan, Alireza,Valizadeh, Hassan,Heydari, Akbar,Moghimi, Abolghasem
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p. 2315 - 2319
(2017/10/06)
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- Oxyfunctionalization of the Remote C?H Bonds of Aliphatic Amines by Decatungstate Photocatalysis
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Aliphatic amines, oxygenated at remote positions within the molecule, represent an important class of synthetic building blocks to which there are currently no direct means of access. Reported herein is an efficient and scalable solution that relies upon decatungstate photocatalysis under acidic conditions using either H2O2 or O2 as the terminal oxidant. By using these reaction conditions a series of simple and unbiased aliphatic amine starting materials can be oxidized to value-added ketone products. Lastly, NMR spectroscopy using in situ LED-irradiated samples was utilized to monitor the kinetics of the reaction, thus enabling direct translation of the reaction into flow.
- Schultz, Danielle M.,Lévesque, Fran?ois,DiRocco, Daniel A.,Reibarkh, Mikhail,Ji, Yining,Joyce, Leo A.,Dropinski, James F.,Sheng, Huaming,Sherry, Benjamin D.,Davies, Ian W.
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p. 15274 - 15278
(2017/11/01)
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- Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines
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Diverse N,N,O-trisubstituted hydroxylamines, an under-represented group in compound collections, are readily prepared by partial reduction of N-acyloxy secondary amines with diisobutylaluminum hydride followed by acetylation and reduction of the so-formed O-acyl-N,N-disubstituted hydroxylamines with triethylsilane and boron trifluoride etherate. Use of carbon nucleophiles in the last step, including allyltributylstannane, silyl enol ethers, and 2-methylfuran, gives N,N,O-trisubstituted hydroxylamines with branching α- to the O-substituent. N,N-Disubstiuted hydroxylamines are conveniently prepared by reaction of secondary amines with dibenzoyl peroxide followed by diisobutylaluminum hydride reduction.
- Dhanju, Sandeep,Crich, David
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supporting information
p. 1820 - 1823
(2016/05/19)
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- MACROCYCLES AND THEIR USES
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The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases
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- New conformationally locked bicyclic N,O-nucleoside analogues of antiviral drugs
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In order to obtain rigidity within the sugar moiety of nucleosides, the bicyclic pyrimidine derivatives of N,O-isoxazolidines were designed and synthesized by using 1,3-dipolar cycloaddition of Δ1- pyrrolidine-1-oxide and the appropriate vinyl-nucleobases.
- Procopio, Antonio,Alcaro, Stefano,De Nino, Antonio,Maiuolo, Loredana,Ortuso, Francesco,Sindona, Giovanni
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p. 545 - 550
(2007/10/03)
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- Low molecular weight bicyclic thrombin inhibitors
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This invention relates to the discovery of heterocyclic competitive inhibitors of the enzyme thrombin, their preparation, and pharmaceutical compositions thereof. As well, this invention relates to the use of such compounds and compositions in vitro as anticoagulants and in vivo as agents for the treatment and prophylaxis of thrombotic disorders such as venous thrombosis, pulmonary embolism and arterial thrombosis resulting in acute ischemic events such as myocardial infarction or cerebral infarction. Moreover, these compounds and compositions have therapeutic utility for the prevention and treatment of coagulopathies associated with coronary bypass operations as well as restenotic events following transluminal angioplasty.
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- NEW SYNTHESIS OF (METHOXYCARBONYL)-INDOLIZIDIN-7-ONE AND -QUINOLIZIDIN-2-ONE: AN ACCESS TO β-AMINO ACIDS WITH INDOLIZIDINE AND QUINOLIZIDINE BACKBONE
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Two protected β-amino acids containing the indolizidine or quinolizidine skeleton have been synthesised.The key step of the strategy is represented by the new synthesis of indolizidinone and quinolizidone II carried out by the opening of the tricyclic 1,3-dipolar cycloaddition products 17 or 18 with DABCO.A new and more convenient method for the synthesis of the cyclic hydroxylamines 13 and 14 precursors of nitrones is also reported.
- Cordero, Franca M.,Machetti, Fabrizio,Sarlo, Francesco De,Brandi, Alberto
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- Angiotensin II receptor blocking 2,3,6 substituted quinazolinones
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This disclosure describes novel 2, 3, 6 substituted quinazolinones having the formula: STR1 wherein X, R, and R 6 are described in the specification which have activity as angiotensin II (AII) antagonists.
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- Angiotensin II receptor blocking 2, 3, 6 substituted quinazolinones
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This disclosure describes novel 2,3,6, substituted quinazolinones of the formula: STR1 wherein R 1, R 6 and X are described in the specification which have activity as angiotensin II (AII) antagonistis.
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- Process for the preparation of 3-pyrrolidinols and intermediates therefor
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3-Pyrrolidinol or its salt is economically produced by cyclizing an aminobutanol derivative of the formula: STR1 wherein R is an alkyl or a substituted or unsubstituted phenyl group, or its salt.
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- Analgesic 1-oxa-, aza- and thia-spirocyclic compounds
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Mono-Oxa-, thiaspirocyclic-benzene-acetamide and -benzamide compounds of the formula STR1 wherein p, n, m, A, E, R, R1, R2, X, Y and Z are as defined in the specification, e.g., (±)-(5α,7α,9β)-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide, and the pharmacologically acceptable salts thereof, are useful as analgesic compounds having low physical dependence liability, compared to morphine and methodone, and low dysphoria side effects. Some of these compounds have potent analgesic activity when administered orally, and some have low CNS sedative side effects. Pharmaceutical compositions and methods for using these compounds as analgesics are disclosed. Processes for preparing this class of compounds are also disclosed.
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