scholarly journals Novel synthesis of furancarboxylate derivatives via cyclization reactions of (E)-ethyl 3-aryl-2-cyanoacrylates and ethyl glycinate hydrochloride

2020 ◽  
pp. 174751982095959
Author(s):  
Naili Luo ◽  
Shan Wang ◽  
Zhenjie Su ◽  
Cunde Wang
Keyword(s):  
Synthetic Approach ◽  
Cyclization Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Mild Conditions ◽  
Novel Synthesis ◽  
Substituted Furans

An efficient synthetic approach for the preparation of densely substituted furans starting from ( E)-ethyl 3-aryl-2-cyanoacrylates and ethyl glycinate hydrochloride mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene in the presence of water is investigated. The reactions are carried out under mild conditions in N,N-dimethylformamide at 95 °C. The products are cleanly obtained in 50%–57% yields, resulting in an appealing alternative for accessing polysubstituted furan-2,4-dicarboxylates. The structure of a typical product, diethyl 5-amino-3-( p-tolyl)furan-2,4-dicarboxylate, is confirmed by X-ray crystallography.

scholarly journals Rational synthesis of an atomically precise carboncone under mild conditions

2019 ◽  
Vol 5 (8) ◽  
pp. eaaw0982 ◽  
Author(s):  
Zheng-Zhong Zhu ◽  
Zuo-Chang Chen ◽  
Yang-Rong Yao ◽  
Cun-Hao Cui ◽  
Shu-Hui Li ◽  
...  
Keyword(s):  
Apex Angle ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
X Ray ◽  
Carbon Allotropes ◽  
X Ray Crystallography ◽  
Mild Conditions ◽  
Research Opportunity ◽  
Insight Into ◽  
Structural Strain

Carboncones, a special family of all-carbon allotropes, are predicted to have unique properties that distinguish them from fullerenes, carbon nanotubes, and graphenes. Owing to the absence of methods to synthesize atomically well-defined carboncones, however, experimental insight into the nature of pure carboncones has been inaccessible. Herein, we describe a facile synthesis of an atomically well-defined carboncone[1,2] (C70H20) and its soluble penta-mesityl derivative. Identified by x-ray crystallography, the carbon skeleton is a carboncone with the largest possible apex angle. Much of the structural strain is overcome in the final step of converting the bowl-shaped precursor into the rigid carboncone under mild reaction conditions. This work provides a research opportunity for investigations of atomically precise single-layered carboncones having even higher cone walls and/or smaller apex angles.

scholarly journals Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3186 ◽  
Author(s):  
Vasilyev ◽  
Bizyaev ◽  
Komarov ◽  
Gatilov ◽  
Tkachev
Keyword(s):  
Calculated Data ◽  
Transition Metal Ions ◽  
Synthetic Approach ◽  
Spectroscopic Methods ◽  
Aromatic Diamines ◽  
X Ray ◽  
X Ray Crystallography ◽  
Chemical Structures ◽  
Polydentate Ligands ◽  
New Compounds

A synthetic approach to a new group of stable chiral C2-symmetric diimines with the 4,5-diazafluorene core has been developed based on condensation of dipinodiazafluorene with aromatic diamines. The chemical structures of new compounds were proven by spectroscopic methods and X-ray crystallography. All the compounds form solvates with organic solvents (chloroform, benzene, 1,4-dioxane) and water. Specific spectral data of the new compounds are explained using calculated data (DFT). Diimines of the pinodiazafluorene series give colored reactions with transition metal ions and can be regarded as prospective polydentate ligands with interesting luminescent and chiroptical properties.

Studies Directed Towards the Total Synthesis of Anticapsin. X-Ray Crystal-Structure of (1RS,2SR,4RS,5RS,6SR)-5-Hydroxy-2-phthalimido-1-trimethylsilyloxy-bicyclo[2.2.2]octane-2,6-carbolactone

1990 ◽  
Vol 43 (11) ◽  
pp. 1827 ◽  
Author(s):  
MJ Crossley ◽  
TW Hambley ◽  
AW Stamford
Keyword(s):  
Crystal Structure ◽  
Amino Acid ◽  
Total Synthesis ◽  
Synthetic Approach ◽  
Hydrogen Atoms ◽  
Full Matrix ◽  
X Ray ◽  
X Ray Crystallography ◽  
Relative Stereochemistry ◽  
Atomic Parameters

The relative stereochemistry of methyl 2-phthalimido-1- trimethylsilyloxybicyclo[2.2.2]oct-5-ene-2-carboxylate (9) and its 5,6-epoxide (10), intermediates in a synthetic approach to the amino acid antibiotic anticapsin, were established by the TiCl4-mediated cyclization of (10) to the carbolactone (12); the structure of which was proved by single-crystal X-ray crystallography. Full-matrix least- squares refinement of all atomic parameters with individual isotropic thermal parameters for the hydrogen atoms by using 1446 reflections converged at R 0.036. Crystals of (12) are monoclinic, P21/c, a 12.342(3), b 12.239(2), c 13.405(3) Ǻ, β 99.34(2)°, Z 4.

scholarly journals Catalytic Activity of Polynuclear vs. Dinuclear Aroylhydrazone Cu(II) Complexes in Microwave-Assisted Oxidation of Neat Aliphatic and Aromatic Hydrocarbons

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 47 ◽  
Author(s):  
Manas Sutradhar ◽  
Tannistha Barman ◽  
Armando Pombeiro ◽  
Luísa Martins
Keyword(s):  
Catalytic Activity ◽  
Aromatic Hydrocarbons ◽  
Catalytic Performance ◽  
Antiproliferative Agents ◽  
One Dimensional ◽  
X Ray ◽  
X Ray Crystallography ◽  
Mild Conditions ◽  
Microwave Assisted ◽  
Aliphatic And Aromatic Hydrocarbons

One-dimensional (1D) polynuclear Cu(II) complex (1) derived from (5-bromo-2-hydroxybenzylidene)-2-hydroxybenzohydrazide (H2L) is synthesized and characterized by elemental analysis, IR spectroscopy, ESI-MS, and single crystal X-ray crystallography. Its catalytic performance towards the solvent-free microwave-assisted peroxidative oxidation of aliphatic and aromatic hydrocarbons under mild conditions is compared with that of dinuclear Cu(II) complexes (2 and 3) of the same ligand, previously reported as antiproliferative agents. Polymer 1 exhibits the highest activity, either for the oxidation of cyclohexane (leading to overall yields, based on the alkane, of up to 39% of cyclohexanol and cyclohexanone) or towards the oxidation of toluene (selectively affording benzaldehyde up to a 44% yield), after 2 or 2.5 h of irradiation at 80 or 50 °C, respectively.

The relative stabilities of PhE(NH-t-Bu)2 and PhE(μ-N-t-Bu)2EPh (E = As, Sb, and Bi): X-ray structures of {Li2[PhAs(N-t-Bu)2]}2 and PhE(μ-N-t-Bu)2EPh (E = Sb, Bi)

2003 ◽  
Vol 81 (2) ◽  
pp. 169-174 ◽  
Author(s):  
Glen G Briand ◽  
Tristram Chivers ◽  
Masood Parvez
Keyword(s):  
Solid State ◽  
Nmr Spectra ◽  
Phenyl Group ◽  
Synthetic Approach ◽  
Relative Stabilities ◽  
X Ray ◽  
X Ray Crystallography ◽  
In Trans ◽  
C Nmr

The reaction of PhECl2 with 2 equiv of LiHN-t-Bu has been studied for the series E = As, Sb, and Bi to determine the effect of the phenyl group on subsequent amine condensation processes. For PhAsCl2, the metathesis product PhAs(NH-t-Bu)2 4 was obtained as a colourless oil. Similar reactions involving PhECl2, where E = Sb or Bi, yielded the cyclodipnict(III)azanes PhE(μ-N-t-Bu)2EPh 5 (E = Sb) and 6 (E = Bi), respectively. Treatment of 4 with 2 equiv of n-BuLi produced the dilithium salt Li2[PhAs(N-t-Bu)2] 7a. Products 4, 5, 6, and 7a were characterized by 1H, 7Li (7a), and 13C NMR spectra, while 5, 6, and 7a were also structurally characterized by X-ray crystallography. Compound 7a is dimeric in the solid state via intermolecular Li···N and η6-Li···Ph interactions. The cyclodipnict(III)azanes 5 and 6 have similar structures, with the exocyclic phenyl groups in trans positions relative to the E2N2 ring. This synthetic approach provides a new route to the four-membered rings RE(μ-N-t-Bu)2ER (E = Sb, Bi) and the first example of a bis(organyl)cyclodibism(III)azane.Key words: arsenic, antimony, bismuth, amides, imides.

Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 885-889 ◽  
Author(s):  
Oualid Talhi ◽  
Artur Silva ◽  
Abdelghani Bouchama ◽  
Ridha Hassaine ◽  
Nadia Taibi ◽  
...  
Keyword(s):  
Room Temperature ◽  
Amino Group ◽  
Conjugate Additions ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
Tandem Process ◽  
Tandem Synthesis

We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleo­philic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane-1,2-diamine to the α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.

The Chemistry of Ethyl 2-Ethoxycarbonyl-5,5-Diphenylpenta-2,3,4-Trienoate, a Potential Precursor of Ph2c=C=C=C=C=O

1987 ◽  
Vol 40 (10) ◽  
pp. 1675 ◽  
Author(s):  
NR Browne ◽  
RFC Brown ◽  
FW Eastwood ◽  
GD Fallon
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Wittig Reaction ◽  
Cyclization Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Concentrated Sulfuric Acid ◽  
Triphenylphosphonium Bromide ◽  
Hydrolysis Of ◽  
Potential Precursor

The title diester , Ph2C=C=C=C( COOEt )2 (2), has been prepared by a Wittig reaction between (2-bromo-3,3-diphenylprop-2-en-1-yl) triphenylphosphonium bromide and diethyl 2-oxopropane-1,3-dioate ( mesoxalic ester). The diester (2) undergoes cyclization reactions in concentrated sulfuric acid to give diethyl 2-(3'-phenyl-1H-inden-1'-y1idene)propane-l,3-dioate (4) and triethyl 3-oxo-3',9-diphenyl-2,3-dihydrospiro[lH-fluorene-1,l'-[1H]indene]-2,2,4-tricarboxylate (6), the structure of which was determined by X-ray crystallography. The title diester (2)adds cyclopentadiene across the 2,3-C=C bond to give diethyl 3-(2',2'-diphenylethenylidene)bicyclo[2.2.l]hept-5-ene-2,2-dicarboxylate (10). Alkaline hydrolysis of diester (10) gives an unstable colourless acid and a stable yellow crypto acid shown by X-ray crystallography to be 3-(2',2'-diphenylethenyl)bicyclo[2.2.l]hepta-2,5-diene-2-carboxylic acid (12). Attempts to convert diesters (2) and acid (12) into derivatives suitable for pyrolytic generation of Ph2C=C=C=C=C=O failed; The mono-acid chloride (14) yielded a small phenylazulene fraction on pyrolysis at 780-800°/0.02 mm.

scholarly journals Novel synthesis of highly functionalized cyclopentane derivatives via [3 + 2] cycloaddition reactions of donor–acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates

2019 ◽  
Vol 43 (1-2) ◽  
pp. 43-49 ◽  
Author(s):  
Chenlu Dai ◽  
Mingshuang Li ◽  
Mengjun Chen ◽  
Naili Luo ◽  
Cunde Wang
Keyword(s):  
Cycloaddition Reaction ◽  
Cycloaddition Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Novel Synthesis ◽  
Donor Acceptor

An efficient [3 + 2] cycloaddition reaction of cyanocyclopropanecarbonates and ( E)-3-aryl-2-cyanoacrylates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene for the synthesis of highly functionalized cyclopentane derivatives in moderate to good yields (79%−87%) was developed. The structures of two typical products were confirmed by X-ray crystallography.

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