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1.
2.
Synthesis of Novel 2-Aminothiophene-3-carboxylates by Variations of the Gewald Reaction 总被引:1,自引:0,他引:1
Hans-Peter Buchstaller Carsten D. Siebert Ralf H. Lyssy Ina Frank Adil Duran Rudolf Gottschlich Christian R. Noe 《Monatshefte für Chemie / Chemical Monthly》2001,132(2):279-293
Summary. The synthesis of the title compounds through variations of the Gewald reaction is presented. Knoevenagel condensation of methylketone derivatives with methyl cyanoacetate and subsequent treatment of the α,β-unsaturated nitriles
with sulfur and amine resulted in the corresponding 2-aminothiophenes 5 or isomers 9 and 10. Reaction of methylketone derivatives bearing a leaving group at the methyl group under modified Gewald conditions selectively led to the formation of 4-substituted 2-aminothiophenes 9a and 12. The introduction of the sulfur atom occurs through nucleophilic displacement with sodium sulfide.
Received July 5, 2000. Accepted (revised) August 23, 2000 相似文献
3.
Summary. A macrocyclic diazadioxa dibromo compound was synthesized by ring closure of 1,2-bis-(2-iodoethoxy)-4,5-dibromo-benzene and 1,4-bis-(p-tolylsulfonyl)-ethylenediamine. Its phthalonitrile derivative was obtained by cyano substitution. This diazadioxa macrocyclic
dibromo derivative was directly converted into the copper(II) phthalocyanine by reaction with CuCN in tetramethyl urea. Conversion
of this phthalonitrile derivative into the metal-free phthalocyanine was accomplished by refluxing with DBU. The zinc(II) phthalocyanine was prepared by reaction of the dinitrile derivative with Zn(OAc)2 in quinoline. The lutetium bis-(phthalocyaninate) complex was obtained by treating the dinitrile derivative with anhydrous lutetium acetate and DBU in 1-hexanol. The new compounds were characterized by elemental analyses and IR, 1H NMR, mass, UV/Vis, and ESR spectra.
Received May 8, 2001. Accepted (revised) June 25, 2001 相似文献
4.
The iodine-azide reaction induced by eight thiosemicarbazones was investigated. Inducing properties of thiosemicarbazones
are different and depend on the parent carbonyl compound used for synthesis. The inductor coefficients of the examined thiosemicarbazones
vary from 61 to 176. Optimum conditions for the determination of microamounts of thiosemicarbazones are given. The detection
limit for the determination by the back-titration method depends on the inducing activity and is 0.9 μg for phenyl-thiosemicarbazones
and 2 μg for diethyl-thiosemicarbazone in a 5-mL sample, and this corresponds to a concentration of 0.9 × 10−6 mol/L and , respectively. The automatic titration with the diluted iodine solution decreases the detection limit to about 50 ng in a
10-mL sample.
Received October 28, 1998. Revision April 9, 1999. 相似文献
5.
Süleyman Gürsoy Zehra A. Bayır Esin Hamuryudan Özer Bekarogğlu 《Monatshefte für Chemie / Chemical Monthly》2000,131(3):287-292
Summary. Unsymmetric metallophthalocyanines (M=Zn, Co, Ni) carrying alkylthio and acetyloxyethylthio groups on peripheral positions were prepared from 4,5-bis-alkylthio-phthalonitrile, 4,5-bis-(acetyloxyethylthio)-phthalonitrile, and the corresponding anhydrous metal salts Zn(CH3COO)2, NiCl2, and CoCl2. The extremely soluble compounds were characterized by their IR, 1H NMR, and UV/Vis spectra. Their long wavelength absorption band was found to be bathochromically shifted; their solubility
is superior to that of symmetrical phthalocyanines.
Received July 27, 1999. Accepted (revised) September 30, 1999 相似文献
6.
Süleyman Gürsoy Makbule Koçak Özer Bekaroğlu 《Monatshefte für Chemie / Chemical Monthly》2000,131(2):181-185
Summary. Platinum and palladium dichlorides react readily with 2,2′-azoquinoxaline to give the di-μ-chloro-2,2′-azobis-(7,7′-bis-benzoyl-quinoxaline)
diplatinum(II) and dipalladium(II) complexes. These crystalline complexes exhibit both metal-carbon binding and coordinate
metal-nitrogene binding to azoquinoxaline.
Received July 16, 1999. Accepted (revised) October 22, 1999 相似文献
7.
Süleyman Gürsoy Ali Cihan Makbule B. Koçak Oüzer Bekaroğlu 《Monatshefte für Chemie / Chemical Monthly》2001,132(7):813-819
Summary. A novel phthalodinitrile derivative carrying dimethylaminoethylsulfanyl groups at positions 4 and 5 was synthesized from
2-dimethylaminoethanethiol hydrochloride and 1,2-dichloro-4,5-dicyanobenzene. Its cyclotetramerization in the presence of
2-dimethylamino-ethanol or metal salts (CoCl2, Zn(OAc)2) gave metal-free or metal-containing phthalocyanines (M = Co or Zn). These phthalocyanines were converted into water soluble quaternized products by reaction with methyl iodide.
The new compounds were characterized by elemental analysis, IR, NMR, and electronic spectra. 相似文献
8.
Abd El-Wareth A. O. Sarhan Makoto Murakami Taeko Izumi 《Monatshefte für Chemie / Chemical Monthly》2002,133(8):1055-1066
Summary. A number of π-extended conjugated tetrathiafulvalene (TTF) analogues were synthesized as new π-donors, and their structures and physical properties were determined. UV/Vis spectra
and cyclic voltammetry of the π-extended ferrocenyl donors were studied in comparison with ferrocene, ferrocenylquinone, and
the parent donor. A three-electron redox behaviour was observed. The absorption spectrum of the new donor 16 showed a slight red-shift and a slight increase in intensity relative to the compared compounds.
Received September 19, 2001. Accepted (revised) October 23, 2001 相似文献
9.
Kenji Yamagata Fumi Okabe Motoyoshi Yamazaki 《Monatshefte für Chemie / Chemical Monthly》2001,132(6):721-729
Summary. The reaction of 4-amino-2,5-dihydro-2- and -5-methyl-3-thiophenecarbonitriles with α-diazocarbonyl compounds in the presence
of rhodium(II) acetate gave regioselectively 4-cyano-2H-thiopyrans (C2-S insertion) in moderate to good yields; 5-cyano-2H-thiopyrans (C5-S insertion) were not isolated. The starting compounds were synthesized by reaction of tetrahydro-2- and -5-methyl-4-oxo-3-thiophenecarbonitriles
with morpholine, piperidine, and pyrrolidine in the presence of formic acid in ethanol.
Received November 13, 2000. Accepted December 12, 2000 相似文献
10.
Summary. N′-Arylacetonitrilimines were generated from acetohydrazonyl chlorides and reacted with mercaptoalkanoic acids forming 4-aryl-5-oxo-3-thiahexanoic
acids. These were cyclized by reaction with dicyclohexyl carbodiimide yielding 2-acetyl-4-aryl-6H-1,3,4-thiadiazin-5-ones.
Received November 13, 2001. Accepted January 9, 2002 相似文献
11.
Zorica M. Bugarčić Biljana Mojsilović Ljiljana Marjanović Stanimir Konstantinović 《Monatshefte für Chemie / Chemical Monthly》2000,131(10):1091-1096
Summary. The reaction of some alkenols with tetrachloromethane in the presence of a radical initiator was investigated. Regarding
the effects of structural features of the starting alkenol (number and position of methyl substituents at the double bond
and at the carbinol carbon atom, constitutional relationship between the double bond and the hydroxyl group) there are two
possible competing reactions: addition and cyclization. In the case of the simplest alkenols (without substituents and with
a more remote double bond) addition occurs; mono- and disubstituted secondary and tertiary Δ4- and Δ5-alkenols cyclize in high yields to give the corresponding cyclic ethers.
Received March 17, 2000. Accepted (revised) May 31, 2000 相似文献
12.
Samuel González-Mancebo Javier Lacadena Yolanda García-Alonso Jesús Hernández-Benito Emilio Calle Julio Casado 《Monatshefte für Chemie / Chemical Monthly》2002,133(2):157-166
Summary. Nitrosation reactions of phenol, o-cresol, 2,6-dimethylphenol, o-tert-butylphenol, 2-hydroxyacetophenone, and 2-allylphenol in water and water/acetonitrile were studied. Kinetic monitoring of
the reactions was accomplished by spectrophotometric analysis of the nitrosated products at 345 nm. The dominant reaction
was C-nitrosation via a mechanism consisting of an attack on the nitrosatable substrate by NO+/NO2H2
+ followed by a slow proton transfer. The values of the rate constants of phenolic C-nitrosation were increased by electron
donating substituents, and a good Hammett correlation was observed with ρ = −6.1. The results also revealed the strong effect of pH and the permitivity of the reaction medium on the rate constant, whose maximum values were observed for pH ≈ 3, decreasing strongly for higher pH values. The study in water/acetonitrile with up to 25% acetonitrile showed that it is possible to inhibit the reaction strongly
by increasing the percentage of the organic component. The conclusions drawn show that (i) it is possible to predict the rate of nitrosation of phenolics as a function of the meta-substituents on the phenol ring and (ii) the nitrosation of phenolics can be strongly inhibited by increasing the pH of the reaction medium as well as by lowering its dielectric constant.
Received July 13, 2001. Accepted (revised) September 18, 2001 相似文献
13.
Roland A. Obermüller Thomas G. Dax Heinz Falk 《Monatshefte für Chemie / Chemical Monthly》2001,132(9):1057-1062
Summary. When 1-methoxy-2-naphthalene carboxylic acid diethylamide was reacted with tert-butyl lithium in presence of TMEDA and 3,5-dimethoxybenzaldehyde was subsequently added to the reaction mixture, (P, S/M, R)- and (P, R/M, S)-1-tert-butyl-3-((3,5-dimethoxyphenyl)-hydroxymethyl)-naphthalene-2-carboxylic acid diethylamide were formed instead of the corresponding
1-methoxy derivative. The diastereomeric relationship of the products is due to a sterically severely hindered rotation around
the amide-aryl bond.
Received May 11, 2001. Accepted May 18, 2001 相似文献
14.
Jozef Saloň Viktor Milata Nadežda Prónayová Ján Leško 《Monatshefte für Chemie / Chemical Monthly》2000,131(3):293-299
Summary. Reaction of 5-aminoquinoxaline with alkoxymethylene derivatives affords the corresponding quinoxalinoaminoethylenes. These
undergo a thermal cyclization to yield angularly annelated 10H-pyrido[2,3-f]quinoxalines. The structures of all products were deduced from their IR, UV, mass, 1H, and 13C NMR spectra.
Received September 24, 1999. Accepted November 18, 1999 相似文献
15.
Mazaahir Kidwai Preeti Misra Bhavesh Dave Kumar R. Bhushan Rajendra K. Saxena Meena Singh 《Monatshefte für Chemie / Chemical Monthly》2000,131(11):1207-1212
Summary. A novel synthesis of 6-fluoro-7-(5-aryl-1,3,4-thiadiazol/oxadiazol-2-yl-sulfanyl)-4-quinolone-3-carboxylic acids from 7-chloro-6-fluoro-4-quinolone-3-carboxylic
acid and 5-substituted 1,3,4-thiadiazoles/oxadiazoles on basic alumina under microwave activation is described. All compounds
were screened for their in vitro antibacterial activity against B. lichenformis, 2689, K. aerogens 2281, S. typhimurium 2501, E. herbicola 2491, and P. vulgaris 2027 and found to possess activities comparable to that of the standard drug norfloxacin.
Received May 2, 2000. Accepted (revised) June 13, 2000 相似文献
16.
Rafat M. Mohareb Fatma A. Al-Omran Jonathan Z. Ho 《Monatshefte für Chemie / Chemical Monthly》2002,133(11):1443-1452
Summary. 2-Amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with ethyl β-amino-α-cyano-γ-ethoxycarbonylcrotenoate yields the corresponding amide derivative. That compound
reacts with benzenediazonium chloride to give the phenyl hydrazone derivative. This type of compounds was cyclized to give
pyridazine and pyridine derivatives, respectively. Chemical reactivities of the latter were studied to give fused heterocyclic
compounds with antimicrobial activities.
Corresponding author. E-mail: rmmohareb@hotmail.com
Received February 8, 2002; accepted (revised) March 28, 2002 相似文献
17.
Eatedal H. Abdel Aal Osama I. El-Sabbagh Shaker Youssif Sameh M. El-Nabtity 《Monatshefte für Chemie / Chemical Monthly》2002,133(3):255-266
Summary. New benzenesulfonamide derivatives containing pyrazole and oxadiazole moieties were prepared starting from sodium saccharin.
The structures of the novel compounds were characterized by elemental analyses and spectroscopic methods. The new compounds
are structurally related to the COX-2 inhibitor celecoxib (Celebrex?). A pharmacological study of the pyrazoles revealed that several compounds possess higher analgesic and antiinflammatory
activities than celecoxib, particularly 11 and 17. Most of the pyrazoles showed a significant increase in the sleeping time of thiopentone anaesthesized mice and also protected
mice against the convulsive and lethal effects of pentylenetetrazole. Moreover, the ulcerogenic activity of those compounds
showing a pronounced antiinflammatory effect was also studied.
Received August 20, 2001. Accepted (revised) November 19, 2001 相似文献
18.
Jarosłlaw Lewkowski Jacques Mortier Michel Vaultier 《Monatshefte für Chemie / Chemical Monthly》2000,131(7):707-710
Summary. Reaction of boron tribromide with triethyl phosphite led to the formation of triethyl tribromoborophosphate 1, a complex bearing a P→B bond.
Received November 19, 1999. Accepted (revised) January 21, 2000 相似文献
19.
Kenji Yamagata Fumi Okabe Motoyoshi Yamazaki Yoshinobu Tagawa 《Monatshefte für Chemie / Chemical Monthly》2002,133(5):643-651
Summary. The reaction of 2-amino-4,5-dihydro-3-furancarboxamides with morpholine in the presence of acetic acid in pyridine or under
the influence of ammonium acetate gave the corresponding 3-diaminomethylene-4,5-dihydro-2(3H )-furanones; 4,5-dihydro-2-morpholino-3-furancarboxamides were not isolated. One of the former reacted with benzylamine to
give (E )- and (Z )-3-(amino-(benzylamino)-methylene)-4,5-dihydro-4-phenyl-2(3H )-furanones and 2-benzylamino-4,5-dihydro-4-phenyl-3-furancarboxamide.
Received October 4, 2001. Accepted October 10, 2001 相似文献
20.
Luminita Muntean Ion Grosu Gerard Plé Sorin Mager Ioan Silaghi-Dumitrescu 《Monatshefte für Chemie / Chemical Monthly》2000,131(9):975-983
Summary. The synthesis and the stereochemistry of new spiro-1,3-perhydrooxazines are reported. The stereoisomerism of these compounds
is discussed considering the data of conformational analysis, the helical chirality of the spiro[5.5]undecane skeleton, and
the triligand virtual chiral center belonging to the 1,3-perhydrooxazine ring.
Received February 21, 2000. Accepted (revised) April 18, 2000 相似文献