Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines

1999 ◽  
Vol 54 (7) ◽  
pp. 849-857 ◽  
Author(s):  
Petra Prokop ◽  
Rainer Richter ◽  
Lothar Beyer
Keyword(s):  
Ethyl Ester ◽  
Carbonic Acid ◽  
Acid Ethyl Ester ◽  
Crystal Structure Analysis ◽  
Molecular Structures ◽  
Ferrocene Derivatives ◽  
Primary Aromatic Amines ◽  
New Compounds ◽  
C Nmr ◽  
Phenylene Diamine

Starting from ethyl 2,4-dioxo-4-ferrocenyl-butanoate (1) a series of new ferrocene derivatives has been prepared. While the reaction with o-phenylene diamine leads to two ferrocene-containing heterocyclic compounds, 4-ferrocenyl-3H-1,5-benzodiazepine-2-carbonic acid ethyl ester (3) and 3-(2-ferrocenyl-2-oxo-ethylidene)-3,4-dihydro-1H-quinoxalin-2-one · H20 (4), reactions with m- and p-phenylene diamine give both the mono- and disubstituted products 5 - 8, respectively. The conversion of 4 by Lawesson’s reagent results in 2-ferrocenvl-thieno[2,3- b]quinoxaline (9). The new compounds have been characterized by their 1H, 13C NMR, and mass spectra. The molecular structures of 4-ferrocenyl-4-oxo-2-phenylamino-but-2-enoic acid ethyl ester 2, and of 4 and 9 have been determined by X-ray crystal structure analysis.

scholarly journals New Synthetic Routes for 1-Benzyl-1,4,7,10-tetraazacyclododecane and 1,4,7,10-Tetraazacyclododecane-1-acetic Acid Ethyl Ester, Important Starting Materials for Metal-coded DOTA-Based Affinity Tags

2007 ◽  
Vol 62 (3) ◽  
pp. 397-406 ◽  
Author(s):  
Stephan W. Kohl ◽  
Katharina Kuse ◽  
Markus Hummert ◽  
Herbert Schumann ◽  
Clemens Mügge ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ethyl Ester ◽  
Nmr Spectra ◽  
Acid Ethyl Ester ◽  
Affinity Tags ◽  
X Ray ◽  
H Nmr ◽  
Synthetic Routes ◽  
New Compounds ◽  
C Nmr

Two improved routes to synthesize 1-benzyl-1,4,7,10-tetraazacyclododecane (6) and 1,4,7,10- tetraazacyclododecane-1-acetic acid ethyl ester (11) are described as well as the synthesis of 1-{2-[4-(maleimido-N-propylacetamidobutyl)amino]-2-oxoethyl}-1,4,7,10-tetraazacyclododecane- 4,7,10-triacetic acid (17) and its Y, Ho, Tm, and Lu complexes. The 1H and 13C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of the intermediates 4-benzyl-1,7-bis(p-toluenesulfonyl)diethylenetriamine (3) and 1,4,7-tris(p-toluenesulfonyl)diethylenetriamine (7) are reported and discussed. The rare earth complexes of 17 have been characterized by 1H NMR spectroscopy and MALDI-TOF mass spectrometry.

Synthesis and Characterization of Some New 2-Hydroxy-N-(3-Trifluoromethyl-Phenyl)-Benzamide Derivatives

2008 ◽  
Vol 59 (1) ◽  
pp. 56-60
Author(s):  
Ioana M.c. Ienascu ◽  
Alfa X. Lupea ◽  
Iuliana M. Popescu ◽  
Stefan Th. Tomas ◽  
Alina D. Zamfir
Keyword(s):  
Acetic Acid ◽  
Ethyl Ester ◽  
13C Nmr ◽  
Acid Ethyl Ester ◽  
Synthesis And Characterization ◽  
Chemical Methods ◽  
Physico Chemical ◽  
New Compounds ◽  
Benzamide Derivatives

In the reaction between 2-hydroxy-N-(3-trifluoromethyl-phenyl)-benzamide and chloro-acetic acid ethyl ester, [2-(3-trifluoromethyl-phenylcarbamoyl)-phenoxy]-acetic acid ethyl ester was obtained. The ethyl ester was condensed with hydrazine giving 2-hydrazinocarbonylmethoxy-N-(3-trifluoromethyl-phenyl)-benzamide. This hydrazide is considered the key intermediate for the synthesis of new compounds. So, in the reaction between hydrazide and chloro-substituted benzaldehydes hydrazones were obtained. In order to establish their structures, all new synthesized compounds were analyzed by modern physico-chemical methods (FTIR, 1H-NMR, 13C-NMR, MS).

1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadien-1,2,3,4-tetrayl)tetrakis} ]-(4,1-phenylen)-alkanone und deren Natrium-, Thallium(I)- und Fe(II)-Komplexe / 1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadiene-1,2,3,4-tetrayl)tetrakis} ](4,1 -phenylene)-alkanones and their Sodium, Thallium(I) and Iron(II) Complexes

1993 ◽  
Vol 48 (3) ◽  
pp. 297-312 ◽  
Author(s):  
Herbert Schumann ◽  
Andreas Kucht ◽  
Homa Kucht ◽  
Alexander Lentz ◽  
Lothar Esser ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Sodium Salt ◽  
Nmr Spectra ◽  
Ferrocene Derivatives ◽  
X Ray ◽  
New Compounds ◽  
C Nmr

Tetraphenylcyclopentadiene (1) reacts with acylchlorides RC(O)Cl (R = CH3, C3H7, C5H11,C7H15) to form the corresponding [(cyclopentadiene tetrayl)tetrakis] (4,1-phenylene)alkanones C5H2(C6H4C(O)R-4)4 (2a, 2b, 2c and 2d). 2a reacts with NaNH2 generating the corresponding sodium salt Na[C5H(C6H4C(O)R-4)4] (3a). 2a, 2b, 2c, and 2d react with T1OC2H5 yielding the thallium(I) derivatives Tl[C5H(C6H4C(O)R-4)4] (4a, 4b, 4c, 4d). Octaphenylferrocene (5) reacts with acylchlorides RC(O)Cl (R = CH3, C3H7, C5H11, C7H15) to form octaacylated ferrocenes Fe[C5H(C6H4C(O)R-4)4]2 (6a, 6b, 6c and 6d). 6a can also be prepared by reacting FeI2 with 3a. 6a reacts with NaOBr yielding Fe[C5H(C6H4C(O)OH-4)4]2 (7), which after reaction with C5H11OH and C7H15OH gives the corresponding octaesters Fe[C5H(C6H4C(O)OR-4)4]2 (8c and 8d). 6a and 6b are reduced by N2H4(H2O) to give Fe[C5H(C6H4CH2R-4)4]2 (11a and 11b). The X-ray crystal structures of tetraphenylcyclopentadiene (2 a), as well as of the partially and totally substituted ferrocene derivatives Fe[C5H(C6H4C(O)CH3-4)4][C5H(C6H4C(O)CH3-4)3(C6H5)] (9), Fe[C5H(C6H4C(O)C3H7-4)(C6H5)3]2 (10) and Fe[C5H(C6H4C4H9-4)4]2 (11b) have been determined. The 1H and 13C NMR spectra of the new compounds are reported and discussed.

Analysis of N—H...O hydrogen bonds in new C(O)—NH—P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database

2013 ◽  
Vol 69 (2) ◽  
pp. 184-194 ◽  
Author(s):  
Mehrdad Pourayoubi ◽  
Maryam Toghraee ◽  
Vladimir Divjakovic ◽  
Arie van der Lee ◽  
Teresa Mancilla Percino ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structure Analysis ◽  
Cambridge Structural Database ◽  
Tetrahedral Environment ◽  
Phosphoric Triamide ◽  
Structural Database ◽  
C And N ◽  
New Compounds ◽  
Phosphoric Triamides ◽  
C Nmr

Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formulaXC(O)NHP(O)Y[X= CF3(1) and CClF2(2),Y= NHCH2C(CH3)2CH2NH] involving a 1,3-diazaphosphorinane ring part, and three 2,6-Cl2C6H3C(O)NHP(O)Z2phosphoric triamides [Z= NHC(CH3)3(3), N(CH3)(C6H11) (4) and N(CH3)(CH2C6H5) (5)]. The characterization was performed by31P{1H},1H,13C NMR, IR spectroscopy besides19F NMR for fluorine containing compounds (1) and (2), and X-ray single-crystal structure analysis for (1), (3), (4) and (5). In each molecule the P atom has a distorted tetrahedral environment. The N atoms bonded to P atom have mainlysp2character with a very slight tendency to a pyramidal coordination for some amido groups. Different types of N—H...O hydrogen bonds have been analyzed for (1), (3), (4) and (5) and 118 other structures (including 194 hydrogen bonds) deposited in the Cambridge Structural Database, containing either C(O)—NH—P(O)[N(C)(C)]2or C(O)—NH—P(O)[NH(C)]2. The participation of NCP—H...O=P [NCP= the nitrogen atom of the C(O)—NH—P(O) fragment], N—H...O=P, N—H...O=C and NCP—H...O=C hydrogen bonds in different hydrogen-bonded motifs are discussed. Moreover, the involvement of the O atoms of C=O or P=O in the [NCP—H][N—H]...O=P, [N—H]2...O=P, [N—H]2...O=C and [N—H]3...O=C groups are considered. A histogram of N...O distances, the distribution of N—H...O angles and the scatterplot of N—H...O anglesversusN...O distances are studied.

scholarly journals Effect of 3-Aminobenzoic Acid Ethyl Ester Methanesulfonate (MS-222) on Quality of Marine Cultured Turbot (Scophthalmus maximus) during Simulated Transport in Water

Fishes ◽  
2021 ◽  
Vol 6 (2) ◽  
pp. 20
Author(s):  
Jie Cao ◽  
Qi Wang ◽  
Jun Mei ◽  
Jing Xie
Keyword(s):  
Dissolved Oxygen ◽  
Ethyl Ester ◽  
Acid Ethyl Ester ◽  
Scophthalmus Maximus ◽  
Ammonia Nitrogen ◽  
Control Group ◽  
Aminobenzoic Acid ◽  
Transport Stress ◽  
Turbot Scophthalmus Maximus

This study evaluated the effect of different concentrations (20, 40 and 60 mg/L) of 3-aminobenzoic acid ethyl ester methanesulfonate (MS-222) on the quality changes in turbot during simulated transport in water. The results showed that the ammonia nitrogen content in the transportation water of each sample increased significantly, and the dissolved oxygen level decreased. The dissolved oxygen content in MS-222-treated samples was higher than that of control group (CK) samples. For turbot flesh quality, simulated transport in water led to a decrease in moisture, fat and protein contents in all samples. The MS-222-treated turbot samples showed higher pH values, glycogen contents, springiness and chewiness values and lower lactic acid contents comparing with the CK samples during simulated transport in water. In addition, the fresh and bitter amino acids in the muscle of turbot increased in each treatment group compared to the non-transported fish at the end of the simulated transport. The results showed that MS-222 treatment could retard the turbot transport stress and improve the quality of turbot during simulated transport in water.

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