C-H Amination of Nitro Aza-Heterocyclic Compounds by Vicarious Nucleophilic Substitution

Synlett ◽  
2021 ◽  
Author(s):  
RuShuang Zhou ◽  
Chun Cai
Keyword(s):  
Reaction Mechanism ◽  
Reaction Time ◽  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Heterocyclic Compounds ◽  
X Ray Diffraction ◽  
Short Reaction Time ◽  
X Ray ◽  
Vicarious Nucleophilic Substitution ◽  
Mild Conditions

This manuscript describes the C-H amination of a variety of nitro aza-heterocyclic compounds by Vicarious Nucleophilic Substitution (VNS) methodology with 4-amino-1,2,4-triazole (ATA). The aminated products were characterized by NMR, MS and single-crystal X-ray diffraction. Among the substrates examined, moderate to excellent yield (30-88%) and good regioselectivity (ortho/para position of the nitro) are exhibited. This protocol offers the advantages of mild conditions, short reaction time (only 2-4 h) with inexpensive, commercially available and less toxic amination reagent, no additional catalysts or reagents needed. Possible reaction mechanism was also discussed.

scholarly journals Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1857
Author(s):  
Jakub Wantulok ◽  
Daniel Swoboda ◽  
Jacek E. Nycz ◽  
Maria Książek ◽  
Joachim Kusz ◽  
...  
Keyword(s):  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Electronic Absorption ◽  
New Products ◽  
Nucleophilic Substitution Of Hydrogen ◽  
X Ray Diffraction ◽  
X Ray ◽  
Vicarious Nucleophilic Substitution ◽  
Nucleophilic Displacement ◽  
Aromatic Hydrogen

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl-5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

Unusual Rearrangement of Naphthalene in the Synthesis of a Novel B8-B8-Bridged Derivative in the [(1,2-C2B9H11)2-3-Co]- Series. X-Ray Structure and 11B NMR Spectra of [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- (CH3)4N+

1997 ◽  
Vol 62 (5) ◽  
pp. 746-751 ◽  
Author(s):  
Andreas Franken ◽  
Jaromír Plešek ◽  
Christiane Nachtigal
Keyword(s):  
Nmr Spectroscopy ◽  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Nmr Spectra ◽  
X Ray Diffraction ◽  
X Ray ◽  
Unusual Rearrangement ◽  
Multinuclear Nmr Spectroscopy ◽  
11B Nmr ◽  
Isolated Compound

On treatment of the [(1,2-C2B9H11)2Co]- ion with naphthalene in presence of AlCl3 a remarkably bridged [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- ion is obtained as a single isolated compound. The triatomic -CH2-C9H6- bridge is derived from the rearranged naphthalene nucleus. The mechanism of this reaction is obscure but it does resemble the "Electrophile-Induced Nucleophilic Substitution" reported earlier. The structure of the compound was established by multinuclear NMR spectroscopy and by single crystal X-ray diffraction.

Thiophene ring-opening reactions IV. Facile generation of novel ethyl 4-hydroxy-6-thioxonicotinate─1,3,4- thiadiazoline hybrids

2021 ◽  
Vol 18 ◽  
Author(s):  
Mohammed M. Abadleh ◽  
Ahmad H. Abdullah ◽  
Jalal A. Zahra ◽  
Salim S. Sabri ◽  
Firas F. Awwadi ◽  
...  
Keyword(s):  
Single Crystal ◽  
Spectral Data ◽  
1H Nmr ◽  
13C Nmr ◽  
Ring Opening ◽  
Thiophene Ring ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Ring Opening Reactions

: A set of triethylammonium 4-oxo-6-pyridinethiolate–1,3,4-thiadiazoline hybrids (3a-e) were prepared via the reaction of ethyl 2-chloro-6-cyclopropyl-3- nitro-4-oxothieno[2,3-b]pyridine- 5-carboxylate (2) with the appropriate thiobenzoyl- hydrazide (1a-e) in acetonitrile and triethylamine. These hybrids were readily converted, under neutral mild conditions, into the corresponding 4-hydroxy-6-thioxopyridine –thiadiazoline hybrids (5a-e). The structures of the latter set are supported by HRMS, 1H NMR and 13C NMR spectral data and further confirmed by single-crystal X-ray diffraction studies. Alkylation of these hybrids in the presence of triethylamine occurred exclusively at the 6-thioxosulfur, yielding the respective 6-sulfanyl derivatives (6a-c).

Syntheses, Characterization and Crystal Structure of Zn (II) Complex Constructed from Ferrocenedicarboxylic Acid

2013 ◽  
Vol 750-752 ◽  
pp. 1104-1108 ◽  
Author(s):  
Feng Rao Lang ◽  
Li Yan You
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Electronic Properties ◽  
Elemental Analysis ◽  
Luminescence Properties ◽  
Dimensional Chain ◽  
X Ray Diffraction ◽  
One Dimensional ◽  
X Ray ◽  
Mild Conditions

The Zn (II) complex [Zn (O2CFcCO2)(H2O)2]H2O was synthesized with ferrocenedicarboxylic acid under mild conditions. Its crystal structure was characterized by elemental analysis, IR data and X-ray diffraction single crystal structure analyses. The Zn (II) coordination units are connected, forming one-dimensional chain. At the meanwhile, the luminescence properties and the electronic properties were determined.

Convenient Synthesis and Molecular Structure of the Cyclometallated Complex [IrCl(H)(C6H4PPh2)(PPh3)2]

2014 ◽  
Vol 69 (11-12) ◽  
pp. 1237-1240 ◽  
Author(s):  
Hans-Christian Böttcher ◽  
Peter Mayer
Keyword(s):  
Molecular Structure ◽  
Reaction Time ◽  
Title Compound ◽  
Room Temperature ◽  
Molar Ratio ◽  
X Ray Diffraction ◽  
Short Reaction Time ◽  
X Ray ◽  
Convenient Synthesis ◽  
Cyclometallated Complex

Abstract The reaction of [{Ir(μ-Cl)(coe)2}2] (coe=cis-cyclooctene) with triphenylphosphane (molar ratio of Ir to P=1 : 3) in dichloromethane at room temperature afforded after a short reaction time the cyclometallated complex [IrCl(H)(C6H4PPh2)(PPh3)2] (1) in almost quantitative yield. The molecular structure of the title compound 1 was determined by an X-ray diffraction study.

Reaction of Thiophosphoryl Trichloride with N,N'-Diphenylthiourea

2007 ◽  
Vol 72 (3) ◽  
pp. 297-306 ◽  
Author(s):  
Lenka Dastychová ◽  
Jiří Příhoda ◽  
Jan Taraba
Keyword(s):  
Nmr Spectroscopy ◽  
Single Crystal ◽  
Heterocyclic Compounds ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
X Ray

New heterocyclic thiophosphoric compounds containing the N-C-N sequence in the ring were prepared by the reaction of thiophosphoryl trichloride (PSCl3) with N,N'-diphenylthiourea. Depending on the reaction conditions, two types of heterocyclic compounds were obtained, namely 2-chloro-1,3-diphenyl-1,3,2λ5-diazaphosphetidine-2,4-dithione (1) and 2-chloro-1,3,5-triphenyl-1,3,5,2λ5-triazaphosphinane-2,4,6-trithione (2). N,N',N″-Triphenylguanidinium chloride (3) was identified in the reaction mixture as a by-product in all cases. The course of reactions was followed by 31P NMR spectroscopy and compound 3 was characterized by single-crystal X-ray diffraction.

Electron Microscopy of Shock Loaded Polycrystalline Beryllium

1974 ◽  
Vol 32 ◽  
pp. 506-507 ◽  
Author(s):  
J. M. Galbraith ◽  
L. E. Murr ◽  
A. L. Stevens
Keyword(s):  
Electron Microscopy ◽  
Wave Propagation ◽  
Structural Change ◽  
Single Crystal ◽  
Diffraction Pattern ◽  
Shock Loading ◽  
Slip Systems ◽  
Compression Tests ◽  
X Ray Diffraction ◽  
X Ray

Uniaxial compression tests and hydrostatic tests at pressures up to 27 kbars have been performed to determine operating slip systems in single crystal and polycrystal1ine beryllium. A recent study has been made of wave propagation in single crystal beryllium by shock loading to selectively activate various slip systems, and this has been followed by a study of wave propagation and spallation in textured, polycrystal1ine beryllium. An alteration in the X-ray diffraction pattern has been noted after shock loading, but this alteration has not yet been correlated with any structural change occurring during shock loading of polycrystal1ine beryllium.This study is being conducted in an effort to characterize the effects of shock loading on textured, polycrystal1ine beryllium. Samples were fabricated from a billet of Kawecki-Berylco hot pressed HP-10 beryllium.

Crystal structure of an inclusion complex between chiral monoaza-15-crown-5 and S(–)-1-phenyl-ethyl ammonium percholorate

2003 ◽  
Vol 218 (5) ◽  
Author(s):  
Süheyla Özbey ◽  
F. B. Kaynak ◽  
M. Toğrul ◽  
N. Demirel ◽  
H. Hoşgören
Keyword(s):  
Crystal Structure ◽  
Inclusion Complex ◽  
Single Crystal ◽  
X Ray Diffraction ◽  
Space Group ◽  
X Ray ◽  
New Type

AbstractA new type of inclusion complex, S(–)-1 phenyl ethyl ammonium percholorate complex of R-(–)-2-ethyl - N - benzyl - 4, 7, 10, 13 - tetraoxa -1- azacyclopentadecane, has been prepared and studied by NMR, IR and single crystal X-ray diffraction techniques. The compound crystallizes in space group

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