- Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3
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A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.
- La, Minh Thanh,Kang, Soosung,Kim, Hee-Kwon
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p. 6689 - 6696
(2019/06/14)
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- Design, synthesis, and biological evaluation of phosphoramide derivatives as urease inhibitors
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The design, synthesis, and biological evaluation of phosphoramide derivatives as urease inhibitors to reduce the loss of ammonia has been carried out. Forty phosphorus derivatives were synthesized and their inhibitory activities evaluated against that of jack bean urease. In addition, in vivo assays have been carried out. All of the compounds were characterized by IR, 1H NMR, MS, and elemental microanalysis. In some cases, detailed molecular modeling studies were carried out, and these highlighted the interaction between the enzyme active center and the compounds and also the characteristics related to their activity as urease inhibitors. According to the IC50 values for in vitro inhibitory activity, 12 compounds showed values below 1 μM and 8 of them represent improvements of activity in comparison to the commercial urease inhibitor N-n-butylthiophosphorictriamide (NBPT) (100 nM) (AGROTAIN). On the basis of the activity results and the conclusions of the molecular modeling study, a structural model for new potential inhibitors has been defined.
- Dominguez, Maria J.,Sanmartin, Carmen,Font, Maria,Palop, Juan A.,San Francisco, Sara,Urrutia, Oscar,Houdusse, Fabrice,Garcia-Mina, Jose M.
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experimental part
p. 3721 - 3731
(2010/03/05)
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- 2-AMINO-1,3,2λ5-OXAZAPHOSPHORINANE 2-OXIDES
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1,3,2λ5- oxazaphosphorinane 2-oxide derivatives were obtained by phosphorylation of amines and amino acid esters.A method for synthesizing pure enantiomers of 2-phenylamino-1,3,2λ5-oxazaphosphorinane 2-oxide was elaborated.
- Uryupin, A. B.,Kadyko, M. I.,Petrovskii, P. V.,Okruszek, A.,Kinas, R.,et al.
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p. 1433 - 1437
(2007/10/03)
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- CONFORMATIONS OF SATURATED SIX-MEMBERED-RING PHOSPHORUS HETEROCYCLES. SYNTHESES AND X-RAY CRYSTAL STRUCTURES OF THREE 2-ANILINO-2-OXO-5,5-DIMETHYL-1,3,2-OXAZAPHOSPHORINANES
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Single-crystal X-ray structural determinations have been made on 2-anilino-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane, 1; 2-(4-fluoroanilino)-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane, 2; and 2-(4-dimethylaminoanilino)-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane, 3.Compounds 1 and 2 are isostructural and crystallize in the monoclinic space group P21/c with four molecules per unit cell.The cell dimensions for 1 are: a = 12.234(4) Angstroem, b = 8.891(3) Angstroem, c = 12.152(4) Angstroem, and B = 110.77(4) deg.The cell dimensions for 2 are: a = 12.505(1) Angstroem, b = 8.919(1) Angstroem, c = 12.211(1) Angstroem, and B = 109.14(1) deg.Compound 3 crystallizes in the monoclinic space group P21/n with four molecules per unit cell of dimensions a = 6.321(2) Angstroem, b = 19.963(3) Angstroem, c = 12.236(2) Angstroem, and B = 104.89(4) deg.Full-matrix least-squares refinement for each of the structures led to conventional R factors of 5.1percent for 1, 4.9percent for 2, and 9.5percent for 3.The conformation adopted by 1 and 2 is the chair conformation with the anilino substituent axial.Compound 3 adopts the alternative chair conformation with an equatorially disposed anilino substituent.Structural variations are found which can be attributed to the operation of exo and endo anomeric effects.
- Bentrude, Wesley G.,Setzer, William N.,Newton, M. Gary,Meehan, Edward J.,Ramli, Emmanuel,et al.
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- Contributions to the Chemistry of Boron, 138. N-Borylated Derivatives of Phosphoric Amides: Examples of Intermolecular Borotropy
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(Phosphorylamino)boranes of the type X2P(O)-NR'-BR2 (1-10) as well as 3B (11) have been prepared by several methods.Monomeric compounds are present in solution for X=R=N(CH3)2 and borotropic isomers X2P(NR')-O-BR2 were detected for X=Cl, N(CH3)2 and R=CH3.The borotropic equilibrium is established intermolecularly via dimers.This equilibrium lies fully on the side of the dimers for X=R=Cl and X=Cl, R=Br, respectively.This was ascertained for 2 (16) by an X-ray structure determination: the monomeric unit dimerizes to a molecule containing an eight-membered ring having a chair-like conformation.
- Noeth, Heinrich,Storch, Wolfgang
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p. 2140 - 2156
(2007/10/02)
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