106881-77-0Relevant articles and documents
Unusual course of the p-nitrophenyl phosphate esters cleavage by 3-hydroxyiminoalkylpyridinium salts in micellar solutions
Kotoucova, Hana,Mazac, Jiri,Cibulka, Radek,Hampl, Frantisek,Liska, Frantisek
, p. 649 - 650 (1998)
Two types of amphiphilic quaternary 3-pyridinium ketoximes with different position of the hydrophobic alkyl chain were synthesized and tested as hydrolytic micellar catalysts. A considerable positive deviation from the expected first-order curve was observed in the absorbance vs time plot when p-nitrophenyl diphenyl phosphate and p-nitrophenyl diethyl phosphate were hydrolyzed in micellar solutions of the prepared ketoximes under pseudo-first-order reaction conditions.
Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 1295 - 1298 (2019/04/13)
A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.
An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
Augustine, John Kallikat,Kumar, Rajesha,Bombrun, Agnes,Mandal, Ashis Baran
experimental part, p. 1074 - 1077 (2011/03/22)
An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.
Modulation of PPAR subtype selectivity. Part 2: Transforming PPARα/γ dual agonist into α selective PPAR agonist through bioisosteric modification
Zaware, Pandurang,Shah, Shailesh R.,Pingali, Harikishore,Makadia, Pankaj,Thube, Baban,Pola, Suresh,Patel, Darshit,Priyadarshini, Priyanka,Suthar, Dinesh,Shah, Maanan,Jamili, Jeevankumar,Sairam, Kalapatapu V.V.M.,Giri, Suresh,Patel, Lala,Patel, Harilal,Sudani, Hareshkumar,Patel, Hiren,Jain, Mukul,Patel, Pankaj,Bahekar, Rajesh
scheme or table, p. 628 - 632 (2011/03/18)
A novel series of oxime containing benzyl-1,3-dioxane-r-2-carboxylic acid derivatives (6a-k) were designed as selective PPARα agonists, through bioisosteric modification in the lipophilic tail region of PPARα/γ dual agonist. Some of the test compounds (6a
Synthesis of highly substituted pyrroles via nucleophilic catalysis
Ngwerume, Simbarashe,Camp, Jason E.
supporting information; experimental part, p. 6271 - 6274 (2010/11/19)
Figure presented. A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activ
Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: Application to the synthesis of nicotine analogues
Huang, Kun,Merced, Francisco G.,Ortiz-Marciales, Margarita,Melendez, Hector J.,Correa, Wildeliz,De Jesus, Melvin
, p. 4017 - 4026 (2008/09/21)
(Chemical Equation Presented) An asymmetric synthesis for the preparation of nonracemic amines bearing heterocyclic and heteroaromatic rings is described. A variety of important enantiopure thionyl and arylalkyl primary amines were afforded by the borane-mediated enantioselective reduction of O-benzyl ketoximes using 10% of catalyst 10 derived from (S)-diphenylvalinol and ethylene glycol with excellent enantioselectivity, in up to 99% ee. The optimal condition for the first asymmetric reduction of 3- and 4-pyridyl-derived O-benzyl ketoxime ethers was achieved using 30% of catalytic loading in dioxane at 10°C. (S)-N-ethylnornicotine (3) was also successfully synthesized from the TIPS-protected (S)-2-amino-2-pyridylethanol in 97% ee.
Enantioselective Strecker-type reaction of phosphinoyl ketimines catalyzed by a chiral Zr-bipyridyldiol catalyst
Chen, Yi-Jing,Chen, Chinpiao
experimental part, p. 2201 - 2209 (2009/04/05)
An enantioselective Strecker reaction of N-diphenylphosphinoyl ketimines with TMSCN employing a chiral zirconium complex formed from chiral bipyridyl diol 1 as catalyst is described. The catalytic efficiency of chiral ligand 1 with other Lewis acids was also explored. Higher yields (50-85%) with moderate to good enantioselectivities (30-80%) were achieved for a variety of N-diphenylphosphinoyl ketimines.
Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist
Chung, John Y. L.,Ho, Guo-Jie,Chartrain, Michel,Roberge, Chris,Zhao, Dalian,Leazer, John,Farr, Roger,Robbins, Micheal,Emerson, Kateeta,Mathre, David J.,McNamara, James M.,Hughes, David L.,Grabowski, Edward J. J.,Reider, Paul J.
, p. 6739 - 6743 (2007/10/03)
A chemoenzymatic synthesis of β3 agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine.
Tetrahydropyridine oxime compounds
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, (2008/06/13)
Certain N-substituted 1-(1,2,3,6-tetrahydro-3-pyridinyl)oximes and N-substituted 1-(1,2,3,6-tetrahydro-4-pyridinyl)oximes are useful as sigma binding agents for the treatment of depression, psychoses and/or inflammatory diseases.
