Silane catecholates: versatile tools for self-assembled dynamic covalent bond chemistry

2019 ◽  
Vol 55 (43) ◽  
pp. 6066-6069 ◽  
Author(s):  
Yoshiteru Kawakami ◽  
Tsuyoshi Ogishima ◽  
Tomoki Kawara ◽  
Shota Yamauchi ◽  
Kazuhiko Okamoto ◽  
...  
Keyword(s):  
Covalent Bond ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Self Assembled

Shape-persistent macrocycles and 3D nanocages have been prepared in one-pot under MeCN-promoted dynamic covalent bond conditions starting from silane catecholates, whose structures were confirmed by X-ray crystallography.

scholarly journals A new one-pot three-component synthesis of 4-aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation

Synthesis ◽  
2021 ◽  
Author(s):  
Muhammad Syafiq Bin Shahari ◽  
Ahmad Junaid ◽  
Edward R. T. Tiekink ◽  
Anton V. Dolzhenko
Keyword(s):  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Antileukemic Activity ◽  
One Pot ◽  
Biological Screening ◽  
X Ray ◽  
X Ray Crystallography ◽  
Cyclic Amines ◽  
Three Component Reaction ◽  
Fast Synthesis

A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) to the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-(3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)-4-phenyl-1,3,5-triazin-2-amine.

Zirconium complexes of a cyclopentadienyl-amido ligand with a pendant amine donor via amine and alkane elimination

1996 ◽  
Vol 74 (9) ◽  
pp. 1696-1703 ◽  
Author(s):  
Ying Mu ◽  
Warren E. Piers ◽  
Donald C. MacQuarrie ◽  
Michael J. Zaworotko
Keyword(s):  
Lewis Acids ◽  
Methyl Chloride ◽  
Monoclinic Space Group ◽  
One Pot ◽  
Amido Complexes ◽  
X Ray ◽  
X Ray Crystallography ◽  
Zirconium Complexes ◽  
Alkane Elimination

Zirconium complexes of the multidentate ligand CpHNMeSiN(H)R (SiNR = -SiMe2N-t-butyl; NMe = -CH2CH2NMe2, 1) were prepared and characterized via amine and alkane elimination procedures. Reaction of 1 with Zr(NMe2)4 gave a mixture of bis-amido complexes 2 in which the ligand was 1,2 and 1,3 substituted. This mixture was converted to the analogous dichlorides 3 using Me2NH•HCl and 1,3-3 was purified at this stage; alternatively, 1,3-3 was obtained in one pot from 1 and Zr(NMe2)4 in ≈70% yield. Conversion of 1,3-3 to dimethyl compound (CpNMeSiNR)Zr(CH3)2, 1,3-4, was accomplished via reaction of the dichloride with methyllithium; methide abstraction with the Lewis acids B(C6F5)3 and [Ph3C]+[B(C6F5)4]− generated the cationic alkyls [(CpNMeSiNR)Zr(CH3)]+[R′B(C6F5)3]− (R′ = CH3, 6a; C6F6, 6b), which were characterized by NMR spectroscopy. Zirconium complexes containing 1 ligated as its 1,2 isomer were obtained from alkane elimination reactions between 1 and in situ prepared RnZrCl4−n (R = CH3, n = 3; R = CH2SiMe3, n = 2). 1,2-3 and the methyl chloride complex 1,2-(CpNMeSiNR)Zr(CH3)Cl, 5, were obtained in 18 and 30% yield, respectively. Complex 5 was characterized by X-ray crystallography (monoclinic, space group P21/a, a = 9.6951(10) Å, b = 14.3794(16) Å, c = 14.364(3) Å, V = 1990.3(5) Å3, Z = 4, R = 0.046, Rw = 0.041.) Key words: amine elimination, Cp-amido, zirconium complexes.

One-pot synthesis of 5-(8-ethoxycarbonyl-1-naphthyl)-10,15,20-triphenyl porphyrin (ENTPP) and spontaneous resolution upon crystallization

2011 ◽  
Vol 15 (03) ◽  
pp. 197-201 ◽  
Author(s):  
Juanxia Yang ◽  
Jiaxun Jiang ◽  
Weiguang Fang ◽  
Xiaoxu Kai ◽  
Chuanjiang Hu ◽  
...  
Keyword(s):  
Soret Band ◽  
Ester Group ◽  
Spontaneous Resolution ◽  
Cd Spectra ◽  
One Pot ◽  
Nmr Spectrum ◽  
X Ray ◽  
X Ray Crystallography ◽  
H Nmr ◽  
Entire Structure

5-(8-ethoxycarbonyl-1-naphthyl)-10,15,20-triphenyl porphyrin (ENTPP) has been synthesized in a one-pot reaction, and the corresponding chiral crystalline samples have been obtained by spontaneous resolution. 1 H NMR spectrum suggests it is mononaphthyl substituted species and an ethyl group is over the porphyrin plane. The structure has been further confirmed by X-ray crystallography. ENTPP·C6H14 (C57H50N4O2 ): monoclinic, P21, a = 10.707(2) Å, b = 12.203(2) Å, c = 17.858(4) Å, β = 103.06(3)°, V = 2272.8(8) Å3, Z = 2. The 8-position substituent, ester group, lies above the porphyrin plane and leads to the conformational chirality. The entire structure is built up with homochiral molecules, which leads to a chiral crystal through packing in P21 space group. Circular dichroism (CD) spectra have exhibited remarkable absorptions in the Soret band region, which further confirms the homochirality of the crystalline samples.

scholarly journals Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

2013 ◽  
Vol 9 ◽  
pp. 2202-2215 ◽  
Author(s):  
Catalin V Maftei ◽  
Elena Fodor ◽  
Peter G Jones ◽  
M Heiko Franz ◽  
Gerhard Kelter ◽  
...  
Keyword(s):  
Natural Product ◽  
Synthesis And Characterization ◽  
Aminobenzoic Acid ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quisqualic Acid ◽  
Oxobutanoic Acid

Taking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.

scholarly journals Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

2014 ◽  
Vol 10 ◽  
pp. 996-1005 ◽  
Author(s):  
G Gangadhararao ◽  
Ramesh Kotikalapudi ◽  
M Nagarjuna Reddy ◽  
K C Kumara Swamy
Keyword(s):  
Single Crystal ◽  
Trifluoroacetic Acid ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Reaction Proceeds ◽  
Propargyl Alcohols

A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence of wet trifluoroacetic acid, in addition to phosphinoylisocoumarins, phosphorus-free isocoumarins were also obtained. Key products were characterized by single crystal X-ray crystallography.

scholarly journals Self-assembled supramolecular cages containing ruthenium(ii) polypyridyl complexes

2015 ◽  
Vol 51 (21) ◽  
pp. 4465-4468 ◽  
Author(s):  
Jiajia Yang ◽  
Mohan Bhadbhade ◽  
William A. Donald ◽  
Hasti Iranmanesh ◽  
Evan G. Moore ◽  
...  
Keyword(s):  
Polypyridyl Complexes ◽  
X Ray ◽  
Esi Ms ◽  
X Ray Crystallography ◽  
Terpyridine Ligands ◽  
Self Assembled

Substitution-inert, redox- and photo-active ruthenium(ii) complexes based on 2,2′,6′,2′′-terpyridine ligands were self-assembled into discrete supramolecular cages via coordination to palladium(ii) centres and characterised by NMR, ESI-MS and X-ray crystallography.

Synthesis and Coordination Chemistry of Doubly-Tridentate Tripodal Pyridazine and Pyrimidine-Derived Ligands: Structural Interplay Between M2L and M2L2 (M = Ni and Pd) Complexes and Magnetic Properties of Iron(II) Complexes

2009 ◽  
Vol 62 (9) ◽  
pp. 1142 ◽  
Author(s):  
Christopher J. Sumby ◽  
Ben A. Leita ◽  
Boujemaa Moubaraki ◽  
Keith S. Murray ◽  
Peter J. Steel
Keyword(s):  
Magnetic Properties ◽  
Coordination Chemistry ◽  
Spin Crossover ◽  
Coordination Complexes ◽  
Planar Geometry ◽  
Tridentate Ligands ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Pd Complexes

The coordination chemistry of three bridging doubly-tridentate ligands, including the known compound 3,6-bis(di-2-pyridylmethyl)pyridazine (1), which is structurally similar to 1,4-bis(di-2-pyridylmethyl)phthalazine (2), and two pyrimidine-linked compounds 4,6-bis(di-2-pyridylmethyl)pyrimidine (3), and 4,6-bis(di-2-pyridylamino)pyrimidine (4), was investigated with FeII, NiII, and PdII metal salts. Ligands 3 and 4 were synthesized in one-pot reactions from easily obtained starting materials; compound 3 was synthesized from di-2-pyridylmethane and 4,6-diiodopyrimidine in 48% yield, while ligand 4 was prepared by reacting di-2-pyridylamine with 4,6-dichloropyrimidine in 27% yield. During the synthesis of 4, an additional compound, 4-chloro-6-(di-2-pyridylamino)pyrimidine (5), with only one tridentate binding site was obtained in 30% yield. Reactions of 1, 3, and 4 with FeII or NiII salts gave two types of complexes, either discrete M2L or M2L2 assemblies. The PdII complexes obtained were also characterized as discrete M2L complexes. The compounds were characterized by a combination of NMR and IR spectroscopy, microanalysis and X-ray crystallography. Noticeable differences in the structures obtained for NiII coordination complexes with the carbon-linked (3) and nitrogen-linked (4) ligands were observed, whereby the nitrogen linker adopted a trigonal planar geometry and prevented tridentate facial coordination of the octahedral metal centres. The magnetic properties of dinuclear FeII complexes of 1 were examined to see if they showed spin-crossover effects, a feature recently observed by others in other dinuclear helicate complexes, but the complexes remained high-spin at all temperatures between 300 and 2 K.

scholarly journals The Novel Polymorphic Form of Bis(3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane) bis(μ4-oxo)-tris(μ3-oxo)-nonakis(μ2-oxo)-nonaaqua-decaoxo-hepta-molybdenum-di-zinc(II) dihydrate, Synthesis, and Properties

2012 ◽  
Vol 2012 ◽  
pp. 1-7
Author(s):  
Rafal Kruszynski ◽  
Tomasz Sieranski ◽  
Bartlomiej Lewinski ◽  
Agata Trzesowska-Kruszynska ◽  
Ewelina Czubacka
Keyword(s):  
Detailed Comparison ◽  
Polymorphic Form ◽  
The Novel ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Zinc Carbonate ◽  
Vis Spectroscopy ◽  
Polymorphic Forms ◽  
Synthesis Procedure

The reaction of molybdophosphoric acid with zinc carbonate followed by addition of hmta leads to formation of a triclinic polymorph of bis(3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane) bis(μ4-oxo)-tris(μ3-oxo)-nonakis(μ2-oxo)-nonaaqua-decaoxo-hepta-molybdenum-di-zinc(II) dihydrate in a one pot simple reaction. The obtained compound has been characterised by IR, UV-Vis spectroscopy, elemental analysis, and X-ray crystallography. A detailed comparison between both polymorphic forms: triclinic a=22.758 Å, b=24.702 Å, c=31.995 Å, α=101.206°, β=103.256°, γ=105.736°, and V=16203.8 Å3 and monoclinic a=43.120 Å, b=12.399 Å, c=16.285 Å, α=90.00°, β=111.12°, γ=90.00°, and V=8122 Å3 was performed. The influence of the synthesis procedure on polymorph formation was described.

NBS mediated one-pot regioselective synthesis of 2,3-disubstituted imidazo[1,2- a ]pyridines and their unambiguous characterization through 2D NMR and X-ray crystallography

Tetrahedron ◽  
2016 ◽  
Vol 72 (27-28) ◽  
pp. 3832-3838 ◽  
Author(s):  
Ranjana Aggarwal ◽  
Gulshan Singh ◽  
Dionisia Sanz ◽  
Rosa M. Claramunt ◽  
M. Carmen Torralba ◽  
...  
Keyword(s):  
2D Nmr ◽  
Regioselective Synthesis ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography

scholarly journals Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione

2021 ◽  
Vol 12 (4) ◽  
pp. 382-388
Author(s):  
Varun Sharma ◽  
Bubun Banerjee ◽  
Aditi Sharma ◽  
Vivek Kumar Gupta
Keyword(s):  
Crystal Structure ◽  
Molecular Docking ◽  
Direct Method ◽  
Docking Studies ◽  
One Pot ◽  
X Ray ◽  
Molecular Docking Studies ◽  
X Ray Crystallography ◽  
Three Component Reaction ◽  
Inhibition Property

The title compound, 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione was synthesized via one-pot pseudo three-component reaction between one equivalent of 5-chloroisatin and two equivalents of 4-hydroxycoumarin using mandelic acid as catalyst in aqueous ethanol at 110 °C. The synthesized compound was characterized by FT-IR, 1H NMR, and HRMS techniques. Single crystals were grown for crystal structure determination by using single X-ray crystallography technique. It was found that the crystals are triclinic with space group P-1 and Z = 1. The crystal structure was solved by direct method and refined by full-matrix least-squares procedures to a final R-value of 0.0688 for 6738 observed reflections. The crystal structure was stabilized by elaborate system of O-H···O, N-H···O, and C-H···O interactions with the formation of supramolecular structures. 3D Hirshfeld surfaces and allied 2D fingerprint plots were analyzed for molecular interactions. Molecular docking studies have been performed to get insights into the inhibition property of this molecule for Human topoisomerase IIα.

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