Hydrazine derivatives in the synthesis of linear and heterocyclic compounds

Кирилин, А. Д.; Belova, L. O.; Гаврилова, А. В.; Korobova, E. A.; Lakhtin, V. G.; Sheludyakov, V. D.

doi:10.1134/s1070363207110126

Cited by 7 publications

(4 citation statements)

References 2 publications

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“…Synthesis, characterization, structure and DFT analysis of compounds HL R,Ph β-Diketone, β-diketimine and β-ketoimine derivatives are conventionally used in coordination chemistry as precursors of monoanionic bidentate κ 2 -O,O′-diketonato, 18 κ 2 -N,N′-diketiminato 19 and κ 2 -O,N-ketoiminato 20 coordinated ligands, respectively. However, compounds of type β-ketohydrazone, I, are much less frequent 21,22 and the number of metal derivatives, II, is quite reduced 23,24 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

et al. 2015

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Ligand precursors HL(R,Ph) (R = Me, Ph) were synthesised by condensation of acetylacetone and the corresponding N,N-substituted hydrazines and were characterised spectroscopically and structurally. Both in the solid state and in solution they behave as (Z)-keto-enehydrazines and this was confirmed by DFT calculations which showed that this form was the most stable of their possible tautomers. The reaction of HL(R,Ph) compounds with copper acetate and nickel acetate in EtOH afforded the corresponding complexes [M(L(R,Ph))2] (M = Cu, Ni; R = Me, Ph). The methyl-substituted derivatives were structurally characterised by X-ray methods. A four-coordinate environment around the metal centre, where the two L(Me,Ph) ligands act as bidentate N,O-chelators and lie in a pseudo-trans conformation, was found for both compounds. The dihedral angle between the two six-membered metallacycles M(L(Me,Ph)) was 0° for nickel, a typical square planar coordination, meanwhile it was 23° for copper, a square planar slightly distorted to pseudotetrahedral coordination. Copper complexes [Cu(L(R,Ph))2] were tested as catalysts, in combination with TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl radical), for the aerobic oxidation of 4-nitrobenzyl alcohol as the model reaction. An almost complete conversion to the corresponding aldehyde was observed after 1 h at 60 °C and 1 bar of dioxygen, in toluene as the solvent. Importantly, air at atmospheric pressure was also observed to be appropriate for the oxidation, although longer reaction times were required. After the optimization of the reaction conditions, the study was extended to other alcohol substrates and good catalytic activity was found for benzylic-type alcohols, while low yield was found for 1-octanol.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

et al. 2015

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“…Hydrazine and hydrazine derivatives, in particular heterocyclic‐substituted hydrazines, are a wide range of useful organic synthons. These compounds enable access to preparation of various 1,2‐diazaheterocycles . Among known heterocycles, the substituted quinolines and heterocyclic‐fused quinoline family represented as one of the distinctive categories in drug design.…”

Section: Introductionmentioning

confidence: 99%

Unanticipated Heterocyclization from Reaction of Hydrazine Hydrate and/or Hydrazine Dihydrochloride with 1‐Ethyl‐4‐hydroxyquinolin‐2(1H)‐one

Hassan

2018

Journal of Heterocyclic Chem

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Unexpectedly, the reaction of 1‐ethyl‐4‐hydroxyquinolin‐2(1H)‐one (1) with hydrazine hydrate and/or hydrazine dihydrochloride led to three different products. In addition to the expected quninolinylhydrazine, two heteropentacycles, diquinopyrrole and diquinopyridazine, were afforded, depending on reaction conditions. The structure of the new products was established upon their spectral and analytical data.

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“…Because of their superior properties 1–3, carbofunctional organosilicon polymers are widely applied in various aspects. For example, they can be chemically modified 4 or associated with other polymers to obtain new materials 5. So they play an important role in organosilicon chemistry 1.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on the mechanism for the thermal rearrangement reactions of 2‐silylethyl acetate H₃SiCH₂CH₂OCOCH₃

Jia

Feng

Song

et al. 2008

Int J of Quantum Chemistry

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The thermal rearrangement mechanisms of 2-silylethylacetate H 3 SiCH 2 CH 2 OOCCH 3 were investigated by ab initio molecular orbital theory for the first time. All structures of reactant, transition states, and products were located and fully optimized at the B3LYP/6-311ϩG(d, p) levels, and harmonic vibrational frequencies for the involved stationary points on the potential energy surface were obtained. The reaction pathways were analyzed and confirmed by intrinsic reaction coordinate (IRC) calculations. Furthermore, atomic charges were determined by using the natural bond orbital (NBO) analysis. The calculational results show that H 3 SiCH 2 CH 2 OOCCH 3 can rearrange thermally in two ways. One is [1,3] rearrangement (Reaction A), in which silyl group transfers from carbon to oxygen(in COOOC) via a four-membered ring transition state, forming silyl acetate and ethylene, the other way, [1,5] rearrangement (Reaction B), happens with transferring of silyl group from carbon to oxygen (in CAO) via a six-membered ring transition state, forming the same products as in Reaction A. The energy barriers of the Reactions A and B were calculated to be 188.9 and 191.6 kJ/mol at the B3LYP/6-311ϩG(d,p) levels, respectively. Changes in thermodynamic functions (⌬S, ⌬H, and ⌬G), equilibrium constant K(T), as well as preexponential factor A(T), and reaction rate constant k(T) in Eyring transition state theory were calculated over a temperature range of 200 -1600 K, and then thermodynamic and kinetic properties of the reactions were analyzed. It can be

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Hydrazine derivatives in the synthesis of linear and heterocyclic compounds

Cited by 7 publications

References 2 publications

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

Unanticipated Heterocyclization from Reaction of Hydrazine Hydrate and/or Hydrazine Dihydrochloride with 1‐Ethyl‐4‐hydroxyquinolin‐2(1H)‐one

Theoretical study on the mechanism for the thermal rearrangement reactions of 2‐silylethyl acetate H₃SiCH₂CH₂OCOCH₃

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Hydrazine derivatives in the synthesis of linear and heterocyclic compounds

Cited by 7 publications

References 2 publications

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols

Unanticipated Heterocyclization from Reaction of Hydrazine Hydrate and/or Hydrazine Dihydrochloride with 1‐Ethyl‐4‐hydroxyquinolin‐2(1H)‐one

Theoretical study on the mechanism for the thermal rearrangement reactions of 2‐silylethyl acetate H3SiCH2CH2OCOCH3

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Theoretical study on the mechanism for the thermal rearrangement reactions of 2‐silylethyl acetate H₃SiCH₂CH₂OCOCH₃