March 2017 Selective Synthesis Dispiro[indoline-3,2′-pyrrolidine-3′,3″-quinoline]
Derivatives and Spiro[imidazole-4,3′-quinoline] Derivatives via
1,3-Dipolar Cycloaddition Reaction
859
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niv am cem
02/
On
e-3 de cycloadditio
structure 4
The target compound 7 was prepared by adding the re- ortion. The poxide for-
ave methyl
© 2016 Wiley Periodicals, Inc. nitrogen atom from sarcosine and carbonyl of isatin, 4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbo for this reaction, leading to the formed spiro
. The nucleophilic reaction between the
Moreover, the treatment of compound 9 w disulphide in the presence of dimethylsulphate g
Chemistry. The 1,3-dipolar cycloaddition reaction of azomethine ylide b with dipolarophile 3 yielded
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We try to synthesize
5′-(4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)-
3′H-spiro[indoline-3,2′-(1,3,4)thiadiazol]-2-one (12) by heating compound 11 with isatin according to literature procedure [18], but this attempt was unsuccessful
(Scheme 3).Figure 1.
13C NMR of compounds 4 and 11.
Scheme 1. Synthesis of 7″-methoxy-4′-(4-methoxyphenyl)-1′-methyl-2″H-dispiro[indoline-3,2′-pyrrolidine-3′,3″-quinoline]-2,2″,4″(1″H)-trione (4).
Scheme 2. Mechanism of formation of 2-amino-7′-methoxy-5-(4-methoxyphenyl)-2′H-spiro[imidazole-4,3′-quinoline]-2′,4′(1′H)-dione (7).
860 W. S. Hamama, A. E. E. Hassanien, M. G. El-Fedawy, and H. H. Zoorob Vol 54
Journal of Heterocyclic Chemi stry DOI 10.1002/jhet
parameters such as heat of formation, electronic energy, nu- clear energy, and dipole moment.
EXPERIMENTAL
Scheme 3. Synthesis of 4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbothiohydrazide (11).
Figure 2. Optimum geometry of intermediate b. [Color figure can be viewed at wileyonlinelibrary.com]
March 2017 Synthesis of Dispiro Spiro Quinoline Derivatives
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Anal. for C28H25N3O5 (483.18): Calcd: C
69.55, H 5.21, N 8.69%. Found: C 69.59, H 5.19, N 8.50%.
2-Amino-7′-methoxy-5-(4-methoxyphenyl)-2′H-spiro[imidazole-
4,3′-quinoline]-2′,4′ (1′H)-dione (7). A mixture of 3 (1.0 g,
3.23mmol), H2O2 (0.37mL, 30%), and ethanol (20mL) was stirred at room temperature then added guanidine nitrate (0.59 g, 4.83mmol) and aqueous solution of KOH
(50%) (1.30mL) were stirred at 80°C for 2 h. The ethanol was evaporated, and water (30mL) was added to the reaction mixture remainder. The outcome product was filtered off, washed accurately with water. The wet product slightly still wet filter cover was mixed with ethanol (10mL), and the resulted suspension refluxed for
30min. After cooling, the precipitate was filtered off, washed with ethanol, and finally dried.
Yellow crystals (0.35 g, 30%), mp 196–197°C (DMF/
H2O); Rf = 0.63 [ethyl acetate: pet. ether (40:60)](1.5:4);
IR(KBr): γ/cm�1 = 3327 (NH2), 3267 (NH), 1658 (CO),
1612 (CONH); 1H NMR (CDCl3): δ: 3.72 (s, 3H, OCH3- quinolone), 3.83 (s, 3H, OCH3-aromatic), 6.77–6.89 (m,
7H, aromatic-CH), 7.87 (broad s, 1H, NH, D2O exchange- able), 9.83 (broad s, 2H, NH2, D2O exchangeable);
This week in lab a Diels-Alder reaction produced 4-cyclohexene-1, 2-dicarboxylic anhydride by combining 1,3 butadiene and maleic anhydride. They reaction basically combined 4 pi electrons from a diene and 2 pi elections from a double bond to produce an alkene ring. The diene must be in s-cis conformation for the reaction to even happen. All of the p-orbitals, both from the diene and the double bond must line up so it can attack from top or bottom, which creates a chair structure. Because of this, the trans conformation is favored due to the lesser steric interactions.
For this lab, certain actions were performed to facilitate the optimal conditions for the Grignard reaction to proceed. As mentioned above, forming the Grignard reagent and the Grignard reaction must take place in dry, anhydrous conditions. This was why the glassware was initially placed in the oven to evaporate any moisture that was present on the glassware. Additionally, the magnesium used in the experiment needed to be dry too, so it was also placed in the oven to be heated. Creating a dry environment was also why the reaction vessel was covered in the septum because it helped prevent the moisture in the air from entering the reaction. Having water in the reaction vessel would destroy the Grignard reagent and hinder the Grignard reaction. Because the reaction needed to be done in dry and anhydrous conditions, diethyl ether was used as the solvent because it was aprotic meaning that the formation of phenylmagnesium bromide and the Grignard reaction would not be hindered by the protonation of water and alcohols3.
In Part 1, ~0.30g of KHP is dissolved in 25.00 mL of water, and titrated with NaOH. The volume of NaOH added to reach the endpoint is recorded and corrected (Table 1). The number of moles of NaOH reacted in trial 1 and trial 2 are 0.001534 mol and 0.001433 mol (Equation 1). The concentration of NaOH in trial 1 and trial 2 are 0.07331 M and 0.06628 M (Equation2). The average concentration of NaOH is 0.06979 M (Equation 3). The average deviation is 0.003515 M (Equation 4). In Part 2, ~0.13g of Na2CO3 is dissolved in 25.00 mL of water, and titrated with HCl. The volume of HCl added to reach the endpoint is recorded and corrected (Table 2). The number of moles of HCl reacted in trial 1 and trial 2 are 0.001225mol and 0.001253mol (Equation 5). The concentration of HCl in trial 1 and trial 2 are 0.03298M and 0. 0.03477M (Equation 6). The average concentration of HCl is
Three types of reaction were conducted, unimolecular nucleophilic substitution reaction (SN1), unimolecular elimination reaction (E1), and bimolecular nucleophilic substitution reaction (SN2). Substitution and elimination reactions are important to allow for the transformation of reactants to desired product. This is extremely important when it comes to synthesis of different molecules for research, commercial, and medical purposes. SN1reaction was to create 2-chloro-2-methylbutane from 2-methyl-2-butanol with a reaction yield of 2.28 g (21.4 mmol) and the reaction product was analyzed by infrared spectroscopy (IR) to determine the purity of 2-chloro-2-mehtlybutane. E1 was to create cyclohexene from cyclohexanol with a reaction yield of 0.17
There are many tests are available to diagnose SLE. The tests available are antinuclear antibody (ANA), complete blood count (CBC), chest x-ray, serum creatinine, and urinalysis [24]. CBC is used to check red blood cells, white blood cells and platelet level which are typically abnormal in patients with SLE [24]. Urinalysis checks for kidney function, measuring the levels of protein and check for any urinal tract infection [68]. A complete physical is also conducted and the heart is checked for abnormal sounds or friction rubbing [24]. To classify a person with SLE, physicians abide to the American College of Rheumatology (ACR) criteria list, in which 4 out of the 12 criteria must be present in a patient and this shows a specificity of 95%
The purpose of this laboratory experiment was to compile data enabling students to classify compounds as ionic or covalent. To do this, students tested the compounds: sodium chloride, calcium chloride, potassium chloride, sucrose, salicylic acid, wax, and stearic acid through their conductivity, solubility, and recorded the order of which the compounds melted. Conductivity was tested by using two paper clips placed in the compounds that were located in water and observing if they were able to charge a closed circuit. Solubility was tested through placing small amounts of the compounds into test tubes and dissolving them with water and the process was repeated with ethanol. The results from this experiment was that the compounds: Sodium Chloride,
My group and I worked on a experiment known as The Mass Mole Relationship in a Chemical Reaction. We investigated that when a chemical reaction occur, then it is possible for us to create a smaller amount than what is expected from the product. We also believed that if there is a 1:1 mole ratio between the reactant and product, then the given number of mole for reactants will be the same number of mole in the products. The purpose of the experiment is to give us a further explanation and understanding on mole mass relationships in a chemical equation and balance chemical equation. It also help us compare the experimental mass of a product of a chemical reaction to the predicted mass of the product.
When the hydrochloric acid (2HCl) and the calcium carbonate (CaCO3) combine it forms calcium chloride (CaCl2) + water (H2O) and carbon dioxide (CO3). This is because the chemical reaction is an acid-base reaction (where an acid + a carbonate (or a hydrogen carbonate) combine to form a salt + water + carbon dioxide) which is specific type of gas evolution reaction (a chemical process that produces a gas, such as oxygen or carbon dioxide). During a chemical reaction the bonds between the atoms in the reactants are broken and to form products that are physically and chemically different from the reactants. In this situation CaCO3 reacts with 2HCl to form CaCl2 and H2CO3, the carbonic acid then decomposes into water and carbon dioxide. When the
Enzymes are protein molecules composed of amino acids and are made by the living cell. These molecules provide energy for the organism by catalyzing various biochemical reactions. If enzymes were not present in cells, most of the chemical reactions would not proceed at measurable rates at the temperatures of living systems. Therefore, we can say that being involved as catalysts is the main and most important role of enzyme in any organism. Many reactions that are thermodynamically favored do not occur quickly because of a lack of energy necessary to initiate the reaction.
The Effect of Heat on Enzyme Reaction: The Effect of Heat, at Varying Temperatures, on the Viability of Biological Enzymes in Pineapple. Introduction: Enzymes are ‘worker’ molecules. They are globular proteins that act as catalysts of chemical reactions.
To begin our experiment, we needed five cuvettes, two flasks, two beakers, glucose, sucrose, lactose, phosphate buffer and ortho-nitro-phenyl-galactoside (ONPG), a lactase pill (our enzyme) and a spectrophotometer.
When nitrate (NO3) has an oxygen molecule removed, it has been reduced to nitrite (NO2).
Introduction The genomic and plasmid DNA are extracted from Escherichia coli, and separated using agarose gel electrophoresis in both non-diluted and 10-fold diluted forms. Charged biomolecules such as DNA, RNA and proteins are separated using agarose gel electrophoresis due to the sieving properties of the agarose. Smaller molecules requires a higher gel concentration with smaller microscopic pores to act as a molecular sieve as they can sieve through faster than larger molecules. In this experiment, the smaller sized plasmid is separated in the 1.0% agarose gel while the larger sized genomic DNA is separated in the 0.7% agarose gel.
Introduction An experiment was conducted to determine how temperature affects enzymatic reactions in four pieces of liver and a potato. During the experiment, a small amount of hydrogen peroxide (2 H2O2), that was heated and cooled to different temperatures was poured onto the liver and potato. The results were then recorded and analyzed to determine how the temperature of the hydrogen peroxide (2 H2O2) affected the rate of the enzymatic reaction. Enzymes are specific molecules that act as organic catalysts and help reduce the amount of energy needed to perform a chemical reaction.
8 R.F. Bis, A. Rodolakis and J. N. Zemel, Rev. Sci. Instrum., 36 (1965) 1626.