- Synthesis of Metallomacrocycle and Coordination Polymers with Pyridine-Based Amidocarboxylate Ligands and Their Catalytic Activities towards the Henry and Knoevenagel Reactions
-
The reactions of 3,3′-{(pyridine-2,6-dicarbonyl)bis(azanediyl)}dibenzoic acid (H2L) with zinc(II), cadmium(II), and samarium(III) nitrates were studied, and the obtained compounds, [Zn(1κO:2κO′-L)(H2O)2]n (1), [
- Karmakar, Anirban,Rúbio, Guilherme M. D. M.,Guedes da Silva, M. Fátima C.,Pombeiro, Armando J. L.
-
p. 865 - 877
(2018/12/10)
-
- Metal-Organic Frameworks with Pyridyl-Based Isophthalic Acid and Their Catalytic Applications in Microwave Assisted Peroxidative Oxidation of Alcohols and Henry Reaction
-
Reactions of 5-{(pyridin-4-ylmethyl)amino} isophthalic acid (H2L1) with copper(II), zinc(II), and cadmium(II) were studied, and the obtained metal-organic frameworks (MOFs) [{Cu(L1)(DMF)}·DMF·H2O]n (1), [Zn(L1)(H2/su
- Karmakar, Anirban,Martins, Luísa M. D. R. S.,Hazra, Susanta,Guedes Da Silva, M. Fátima C.,Pombeiro, Armando J. L.
-
p. 1837 - 1849
(2016/05/09)
-
- A highly diastereo-and enantioselective copper(I)-catalyzed henry reaction using a bis(sulfonamide)-diamine ligand
-
A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantios
- Jin, Wei,Li, Xincheng,Wan, Boshun
-
experimental part
p. 484 - 491
(2011/04/15)
-
- Cyclen-catalyzed Henry reaction under neutral conditions
-
A convenient cyclen-catalyzed Henry reaction of aldehydes with nitroalkanes under mild and neutral conditions is reported. This procedure constitutes the first cyclen-catalyzed synthesis of nitroalcohols and is adapted to the condensation of both aromatic and aliphatic aldehydes with nitromethane in THF at room temperature without addition of stoichiometric amount of the base. A wide range of substrates, β-nitroalcohols, were obtained in moderate to good yields (up to 98%) using this methodology.
- Vovard-Le Bray, Chloé,Jiang, Fan,Wu, Xiao-Feng,Sortais, Jean-Baptiste,Darcel, Christophe
-
supporting information; experimental part
p. 4555 - 4557
(2010/10/02)
-
- Synthesis of new proazaphosphatranes and their application in organic synthesis
-
We report herein the synthesis of the new proazaphosphatrane strong bases P(RNCH2CH2)3N (R=Me3CCH2, Me2CHCH2) and P(HNCH2CH2)2NCH2CH2 N-i-Pr (1g). The new azaphosphatranes [HP(RNCH2CH2)3N]Cl (R=Me3CCH2, Me2CHCH2) have P-Nax distances of 2.047 and 1.958 ?, respectively. We also report the synthesis of the tetramine precursor proazaphosphatrane 1g [namely, (H2NCH2CH2) 2NCH2CH2NH-i-Pr] in 41% yield and the use of a complexation-extraction technique to separate it from a mixture containing the di- and tri-isopropyl substituted analogs. Using a 31P NMR technique, we report the pKa value for 1gH+ (34.49). The catalytic properties of three bases P(RNCH2CH2)3N (R=i-Pr, Piv, i-Bu) are compared in the synthesis of several β-hydroxy nitriles, β-nitroalkanols, α,β-unsaturated esters and for the Michael addition of allyl alcohol to α,β-unsaturated ketones.
- Kisanga, Philip B.,Verkade, John G.
-
p. 467 - 475
(2007/10/03)
-
- P(RNCH2CH2)3N: An Efficient Promoter for the Nitroaldol (Henry) Reaction
-
The use of catalytic amounts of the proazaphosphatranes P(MeNCH2CH2)3N, P(i-PrNCH2CH2)3N and P(HNCH2CH2)(i-PrNCH2CH2) 2N as nonionic bases in the reaction of nitroalkanes with carbonyl compounds is reported. The reaction proceeds at room temperature in the presence of 2.2 equiv of magnesium sulfate to produce the corresponding β-nitroalkanols in generally superior yields. Aldehydes react quantitatively in 5-60 min, whereas ketones require up to 3 h to react with nitromethane and up to 7 h for the reaction of ketones with higher nitroalkanes.
- Kisanga, Philip B.,Verkade, John G.
-
p. 4298 - 4303
(2007/10/03)
-
- Nitroaldol (Henry) reaction catalyzed by amberlyst A-21 as a far superior heterogeneous catalyst
-
β-Nitroalcohols can be efficiently obtained with the help of Amberlyst A-21, as heterogeneous basic catalyst, with or without solvent. This method is far superior to the heterogeneous catalysts previously reported for the nitroaldol (Henry) reaction, in f
- Ballini, Roberto,Bosica, Giovanna,Forconi, Paola
-
p. 1677 - 1684
(2007/10/03)
-
- A new methodology for the preparation of 2-cyanopyrroles and synthesis of porphobilinogen
-
Condensation of α-acetoxynitro compounds 4a-f with isocyanoacetonitrile (5) using DBU in THF afforded 2-cyano-3,4-substituted pyrroles 6a-f, in good yield. Porphobilinogen (PBG, 12), the key building block for the preparation of tetrapyrrolic natural products, was synthesized from 2-cyano-3,4-substituted pyrrole 6f, in four steps.
- Adamczyk, Maciej,Reddy, Rajarathnam E.
-
p. 14689 - 14700
(2007/10/03)
-
- A CONVENIENT SYNTHESIS OF 2-CYANOPYRROLES FROM ISOCYANOACETONITRILE
-
2-Cyano-3,4-substituted pyrroles 2a-e, important intermediates in the synthesis of porphyrins and related compounds, were prepared via base promoted condensation of α-acetoxynitro compound 1a-e with isoacetonitrile (3) in THF, in good yield.
- Adamczyk, Maciej,Reddy, Rajarathnam E.
-
p. 7983 - 7986
(2007/10/02)
-
- Highly efficient nitroaldol reaction promoted by trialkylsilyl chlorides
-
β-Nitroalcohols can be readily obtained in high yields by the one-pot reaction of aldehydes with nitrocompounds in the presence of Et3N, Bu4NF·H2O and (t)BuMe2SiCl. Model experiments indicated that trialkylsilyl
- Fernandez,Gasch,Gomez-Sanchez,Vilchez
-
p. 3225 - 3228
(2007/10/02)
-
- Method of preparing stereospecific nitroaldols
-
A method of controlling the diastereoselectivity of the nitroaldol reaction by the use of titanium, zirconium and aluminum based Lewis acids is disclosed. In a preferred embodiment, the reaction of lithium nitronate anion with aldehydes in THF/CH2/s
- -
-
-
- Dichloroisopropoxytitanium Nitronates as Reagents for Stereoselective Henry Reactions
-
Alkyl nitronates were reacted with aldehydes in the presence of isopropoxytitanium trichloride to give erythro β-nitro alcohols.
- Barrett, Anthony G. M.,Robyr, Chantal,Spilling, Christopher D.
-
p. 1233 - 1234
(2007/10/02)
-
- PREPARATION AND OXIDATION OF α-NITRO ALCOHOLS WITH SUPPORTED REAGENTS.
-
Preparation of 2-nitro alkanols has been achieved by condensation of aldehydes with nitroalkanes in the presence of alumina-supported potassium fluoride.Nitroketones are produced by oxidation of nitroalkanols with montmorillonite - supported chromium trioxide.
- Melot, Jean-Marie,Texier-Boullet, Francoise,Foucaud, Andre
-
p. 493 - 496
(2007/10/02)
-