A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides

2020 ◽  
Vol 44 (4) ◽  
pp. 1253-1262 ◽  
Author(s):  
Mikhail V. Il’in ◽  
Liana A. Lesnikova ◽  
Dmitrii S. Bolotin ◽  
Alexander S. Novikov ◽  
Vitalii V. Suslonov ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
One Pot ◽  
Hydrolytic Reaction

A one-pot route to N-acyl ureas proceeds via generation of electrophilically activated 2-substituted 1,2,4-oxadiazolium salts. The conformation of the N-acyl ureas is stabilized via moderate strength (6.2–7.8 kcal mol−1) resonance-assisted hydrogen bonds.

scholarly journals One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-ethoxycarbonyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate

2018 ◽  
Vol 74 (9) ◽  
pp. 1281-1284
Author(s):  
Thi Thanh Van Tran ◽  
Tuan Anh Le ◽  
Hong Hieu Truong ◽  
Thi Nhung Dao ◽  
Anatoly T. Soldatenkov ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Molecular Conformation ◽  
Michael Reaction ◽  
Biological Activities ◽  
Boat Conformation ◽  
One Pot ◽  
Computer Prediction ◽  
Compound C ◽  
Intramolecular Hydrogen ◽  
The Michael Reaction

The title compound, C30H34N2O9 (4), is a product of the Michael reaction of azacrown ether with dimethyl acetylenedicarboxylate modified by an addition of NH3 (aq.) at 298 K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65 (5)°. The tetrahydropyridine ring has a boat conformation. The molecular conformation is supported by one N—H...O and two C—H...O intramolecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enantiomeric pairs of the 1R,21S diastereomer. In the crystal, molecules of 4 are connected by N—H...O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit antiallergic (72% probability) and antiasthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

scholarly journals DESIGN AND SYNTHESIS OF MOLECULAR TWEEZER BASED ON 3-HYDROXYFLAVONE FOR THE DETECTION OF ATP

2017 ◽  
pp. 67-70
Author(s):  
O. Bugera ◽  
A. Netrebchuk ◽  
V. Pivovarenko
Keyword(s):  
Amino Acid ◽  
Hydrogen Bonds ◽  
Atmospheric Oxygen ◽  
High Sensitivity ◽  
Fluorescence Probes ◽  
Amino Acid Derivative ◽  
One Pot ◽  
Design And Synthesis ◽  
Sensitivity And Selectivity ◽  
Molecular Tweezer

Adenosine 5'-triphosphate (ATP) is known as a universal energy source and signaling mediator in numerous biological processes. Among the methods for its determination, molecular fluorescence probes occupy leading positions due to high sensitivity and selectivity. Recently we have shown that 31 of 33 tested flavones and quinolones of various structures give fluorescence response and can be effectively applied as the probes in aqueous solutions for detection of ATP in 1–50,000 μM range of its concentrations. To increase response parameters of a probe in respect to ATP we have synthesized N,N'-(butane-1,4-diyl)bis(2-((2-(4-(dimethylamino)phenyl)-3-hydroxy-4-oxo-4H-chromene-6-yl)oxy)acetamide, the molecular tweezer composed of two flavonol units connected by active linker. On our idea, being equipped by two planar platforms, the tweezershould demonstrate increased affinity and selectivity to ATP in a result of increased number of hydrogen bonds and increased stacking interactions. Having two NH-amide groups the amino acid linker will form hydrogen bonds with the phosphates of ATP, increasing the portion of probe-ATP complex population in the reporting conformation.In the four-step synthesis of this molecular device, starting from methyl 2-(3-acetyl-4-hydroxyphenoxy)acetate and N,N-dimethylaminobenzaldehyde, the conditions for the reaction of one-pot chalcone formation and its oxidative heterocyclization in the presence of an organic base were found, which resulted in the isolation of a target flavonol-amino acid derivative with high yields. We suggest that atmospheric oxygen was an oxidizer in this process. The obtained derivative was converted intotarget compound by dual condensation with 1,4-butane diamine.

One-Pot Synthesis and Unpredicted Hydrogen Bonds of the Guanidinium Triflates from Readily Available Amines, Carbodiimides, and Zn(OTf)2

2011 ◽  
Vol 30 (19) ◽  
pp. 5278-5283 ◽  
Author(s):  
Dongzhen Li ◽  
Yang Wang ◽  
Wen-Xiong Zhang ◽  
Shaoguang Zhang ◽  
Jie Guang ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
One Pot ◽  
One Pot Synthesis

A pair of 3D enantiotopic zinc(ii) complexes based on two asymmetric achiral ligands

2017 ◽  
Vol 46 (43) ◽  
pp. 14779-14784 ◽  
Author(s):  
Ming-Dao Zhang ◽  
Yan-Le Li ◽  
Zhen-Zhen Shi ◽  
He-Gen Zheng ◽  
Jing Ma
Keyword(s):  
Hydrogen Bonds ◽  
Nonlinear Optical ◽  
Metal Organic Frameworks ◽  
Enantiomeric Excess ◽  
Second Order ◽  
One Pot ◽  
Optical Effects ◽  
Nonlinear Optical Effects ◽  
Metal Organic

Two 3D enantiotopic chiral metal–organic frameworks, with ferroelectric behaviors and second-order nonlinear optical effects, were constructed based on achiral ligands in one pot with high enantiomeric excess owing to the hydrogen bonds.

One-Pot Mechanosynthesis with Three Levels of Molecular Self-Assembly: Coordination Bonds, Hydrogen Bonds and Host–Guest Inclusion

2009 ◽  
Vol 15 (46) ◽  
pp. 12644-12652 ◽  
Author(s):  
Tomislav FrisÌŒcÌŒić ◽  
Ernest MesÌŒtrović ◽  
Dijana SÌŒkalec SÌŒamec ◽  
Branko Kaitner ◽  
László Fábián
Keyword(s):  
Hydrogen Bonds ◽  
Self Assembly ◽  
One Pot ◽  
Coordination Bonds

[Nb6Cl12(HIm)6](OAc)2·3MeOH – a hydrogen-bonded network of niobium cluster cations, acetate anions and methanol molecules

2019 ◽  
Vol 74 (10) ◽  
pp. 751-755
Author(s):  
Eric Sperlich ◽  
Martin Köckerling
Keyword(s):  
Hydrogen Bonds ◽  
Acetic Anhydride ◽  
Title Compound ◽  
Cluster Compound ◽  
Dehydration Reaction ◽  
Coulomb Interactions ◽  
One Pot ◽  
Cluster Precursor ◽  
Additional Hydrogen ◽  
Hydrogen Bonded

AbstractThe new cluster compound [Nb6Cl12(HIm)6](OAc)2 · 3MeOH represents the first example of network compounds consisting of hexanuclear niobium cluster cations and acetate anions, which are connected though hydrogen bonds (besides Coulomb interactions). Hydrogen-bonded cation-anion pairs form chains, which are further extended to sheets by additional hydrogen bonds to co-crystallized methanol molecules. The synthesis of the title compound is based on a one-pot dehydration reaction of the cluster precursor [Nb6Cl14(H2O)4] · 4H2O with acetic anhydride in the presence of imidazole at T = 40°C.

A 2:1 cocrystal of 2,3-bis(4-bromophenyl)quinoxaline and 1,2-bis(4-bromophenyl)ethane-1,2-diol

2006 ◽  
Vol 62 (5) ◽  
pp. o1959-o1960 ◽  
Author(s):  
Liang-Ce Rong ◽  
Xiao-Yue Li ◽  
Chang-Sheng Yao ◽  
Hai-Ying Wang ◽  
Da-Qing Shi
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
One Pot ◽  
X Ray ◽  
Π Interactions ◽  
Compound C ◽  
Low Valent ◽  
The One

The title compound, C20H12Br2N2·0.5C14H12Br2O2, was synthesized by the one-pot reaction of benzofurazan oxide and 1,2-bis(4-bromophenyl)ethane-1,2-dione induced by a low-valent titanium reagent. X-ray analysis reveals that the 1,2-bis(4-bromophenyl)ethane-1,2-diol molecule is located on an inversion centre. The molecules are linked via O—H...N hydrogen bonds and C—H...π interactions.

scholarly journals Crystal structure of [3,10-bis(4-fluorophenethyl)-1,3,5,8,10,12-hexaazacyclotetradecane]nickel(II) diperchlorate

2021 ◽  
Vol 77 (2) ◽  
pp. 148-152
Author(s):  
Chee-Hun Kwak ◽  
Mee Chang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Significant Contribution ◽  
Bond Distance ◽  
Complex Form ◽  
Title Complex ◽  
One Pot ◽  
X Ray ◽  
Square Planar ◽  
Whole Molecule Disorder

The square-planar nickel(II) title complex, [Ni(C24H36F2N6)](ClO4)2 or [NiL](ClO4)2 (L = 3,10-bis(4-fluorophenethyl)-1,3,5,8,10,12-hexaazacyclotetradecane) was synthesized by a one-pot reaction of template condensation and its X-ray crystal structure was determined. The nickel(II) ion lies close by a twofold axis and the complex displays whole-molecule disorder. Ligand L, a hexaazacyclotetradecane ring having 4-fluorophenethyl side chains attached to uncoordinated nitrogen atoms, adopts a trans III (R,R,S,S) configuration. The average Ni—N bond distance is 1.934 (9) Å, which is quite similar to those of other nickel(II) complexes with similar ligands. The nickel(II) ion is located 0.051 (7) Å above the least-squares plane through the four coordinated N atoms. The average C—N bond distance and C—N—C angle involving uncoordinated nitrogen atoms are 1.425 (12) Å and 118.0 (9)°, respectively, indicating a significant contribution of sp 2 hybridization for these N atoms. The intermolecular N—H...O, C—H...O/F hydrogen bonds of the complex form a network structure, which looks like a seamless floral lace pattern.

scholarly journals (C7H6NS)2[Nb6Cl18]·2C4H8O: first niobium cluster with an N,S-heterocyclic cation

IUCrData ◽  
2018 ◽  
Vol 3 (12) ◽  
Author(s):  
Eric Sperlich ◽  
Martin Köckerling
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Room Temperature ◽  
High Yield ◽  
Cluster Compound ◽  
One Pot ◽  
Cluster Precursor ◽  
Acidic Proton ◽  
Very High

The title compound bis(benzothiazolium) dodeca-μ-chlorido-hexachlorido-octahedro-hexaniobium(12 Nb—Nb) tetrahydrofuran disolvate, (C7H6NS)2[Nb6Cl18]·2C4H8O or (HBTh)2[Nb6Cl18]·2THF, is the first known niobium cluster compound to contain an N,S-heterocyclic cation. The synthesis takes place within a few hours as an one-pot reaction at room temperature of the cluster precursor compound [Nb6Cl14(H2O)4]·4H2O with SOCl2 in the presence of BTh (benzothiazole) in very high yield. The stabilization of the acidic proton of the cation is achieved by the use of tetrahydrofuran as a co-solvent and by the formation of hydrogen bonds.

The Structure of Two-Dimensional Layered Cu (ΙΙ) Complex Material

2011 ◽  
Vol 366 ◽  
pp. 392-395
Author(s):  
Xi Shi Tai
Keyword(s):  
Hydrogen Bonds ◽  
Layered Structure ◽  
Sulfonic Acid ◽  
Copper Nitrate ◽  
Monoclinic Space Group ◽  
Two Dimensional ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Π Stacking Interaction

A Cu (II) complex has been obtained by one-pot reaction of copper nitrate with 4-aminobenzene sulfonic acid, 2-acetylpyridine and sodium hydroxide. Unfortunately, the complex does not contain 2-acetylpyridine molecules, and 4-aminobenzene sulfonic acid coordinate to Cu (II) ion. The structure of Cu (II) complex was characterized by single-crystal X-ray diffraction. The results show that the complex crystallizes in monoclinic, space group P2(1)/n with a = 0.7437(3) nm, b = 1.7408(6) nm, c = 0.7644(3) nm, V = 0.8846(5) nm3, Z = 2, F (000) = 494, Rint = 0.0697, and the complex formed two dimensional layered structure through intramolecule and intermolecule hydrogen bonds and π-π stacking interaction.

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