Search results for "medicinal"

ChemInform Abstract: Rearrangements of Nitrile-Stabilized Ammonium Ylides

2014

Rearrangements of nitrile-stabilized ammonium ylides are useful reactions for the construction of alkylamines, nitrogen heterocycles, or carbonyl compounds. In spite of their attractive synthetic potential, they are much less frequently used than rearrangements of ammonium ylides either carrying charge-stabilizing carbonyl groups or being devoid of additional stabilization of the negative charge. This review focuses on different classes of rearrangements of nitrile-stabilized ammonium ylides as well as their application in synthetic organic chemistry. 1 Introduction 2 [1,2]-Stevens Rearrangements 3 [2,3]-Sommelet–Hauser Rearrangement 4 [2,3]-Stevens Rearrangements 5 Competitive [1,2]-, [2,3…

Nucleophilic Additions of the Cyanide Anion to 4,4-Dichloro-1,1-Diphenyl-2-Azabuta-1,3-Diene

2002

The unexpected formation of a 2H-pyrrole by reaction of potassium cyanide with 4,4-dichloro-1,1-diphenyl-2-azabuta-1,3-diene and the mechanism of this reaction are described and the structures of the product and a trapped intermediate confirmed by X-ray crystallographic studies.

Synthese und biochemische Eigenschaften substituierter Phenoxy- und Anilino-1,3,5-triazine

1983

Die nucleophile Substitution eines Chloratoms in 2,4-Dichlor-6-diethylamino-1,3,5-triazin (1) durch die Hydroxyacetophenone 2a–c fuhrt zu den 2-Acetylphenoxy-4-chlor-6-diethylamino-1,3,5-triazinen 3a–c. Analog geht aus der Umsetzung von 1 mit 4-Fluoranilin (4a) das Monoanilinoderivat 5a hervor; dagegen bildet sich unter den gleichen Reaktionsbedingungen aus 1 und 2-Fluoranilin (4b) das Dianilinoderivat 5b. Strukturtyp 3 zeichnet sich durch antimykotische und Antiprotozoenwirksamkeit aus, wahrend 5 herbizide Wirkungen auszulosen vermag. Synthesis and Biochemical Properties of Substituted Phenoxy- and Anilino-1,3,5-triazines The nucleophilic substitution of one chlorine atom in 2,4-dichloro-6…

A DFT study of the [3 + 2] versus [4 + 2] cycloaddition reactions of 1,5,6-trimethylpyrazinium-3-olate with methyl methacrylate.

2013

The reaction between 1,5,6-trimethylpyrazinium-3-olate and methyl methacrylate (MMA) yielding a lactone-lactam has been studied using the DFT method at the B3LYP/6-31G(d) level. It is concluded that formation of the lactone-lactam is a domino process involving three consecutive reactions: (i) a 1,3-dipolar cycloaddition (13DC) reaction between the pyrazinium-3-olate and MMA yielding a [3 + 2] cycloadduct (CA); (ii) a skeletal rearrangement, which converts the [3 + 2] CA into a formal [4 + 2] CA, possessing a diazabicyclo[2.2.2]octane structure; and finally, (iii) an S(N)2 reaction, promoted by halide anion, with concomitant nucleophilic attack of the created carboxylate anion on an iminium …

Redox properties of nitrophenylporphyrins and electrosynthesis of nitrophenyl-linked Zn porphyrin dimers or arrays

2014

Five nitrophenylporphyrins were investigated as to their electrochemical properties in CH 2 Cl 2 containing 0.1 M TBAP. The investigated compounds are represented as ( NO 2 Ph )x Ph 4-x PorM , where Por represents the dianion of the porphyrin macrocycle, Ph is a phenyl group on meso-position of the macrocycle, NO 2 Ph is a meso-substituted nitrophenyl group, M = 2 H , Pd II or Zn II and x = 1 or 2. Each porphyrin undergoes an initial one electron reduction at E1/2 = -1.07 to -1.12 V where the added negative charge is almost totally localized on the meso-nitrophenyl group of the compound. This reversible reduction is then followed by one or more irreversible reductions of the nitrophenyl an…

Mononuclear isoheterocyclic rearrangements. Note I. Interconversion of 3-benzoylamino-5-methyl-1,2,4-oxadiazole and 3-acetylamino-5-phenyl-1,2,4-oxad…

1975

The first example of mononuclear isoheterocyclic rearrangement is reported. The 3-benzoylamino-5-methyl-1,2,4-oxadiazole (5) furnishes through a reversible process (slowly at room temperature in methanol, acetone or dioxane, fast in DMSO or in methanol in the presence of strong bases) a mixture of 5 and 3-acethylamino-5-phenyl-1,2,4-oxadiazole (6). The equilibrium process can be achieved also by heating 5 at 181° and the same reaction mixture can be obtained using 6 as the starting material. 3-Trichloroacetylamino-5-methyl-1,2,4-oxadiazole (7) was unaffected by similar treatment. The results obtained are discussed.

Versuche zum Vorgang der Wasserstoffübertragung, XI. Isomerisierung Definiert Deuterierter Alkylbenzole an Raney-Nickel

1964

α-Deutero-toluol. o-, m- und p-Deutero-toluol sowie β-Deutero-athylbenzol isomerisieren schon bei 20° in Beruhrung mit wasserfreiem Raney-Nickel. Der Deuterium-Gehalt des Substrates bleibt dabei annahernd konstant. Beim α-Deutero-toluol wandern mehr als 50% des Deuteriums aus der Seitenkette in den Kern, wobei es sich weitgehend auf die gleichen Positionen verteilt wie beim Austausch von leichtem Toluol mit Deuterium-Gas an Raney-Nickel. Der aromatische Kern wird unter diesen Bedingungen nicht abgesattigt. Mit Hilfe der Massenspektrographie kann gezeigt werden, das Deuterium auch zwischenmolekular ausgetauscht wird. — Im Toluol kernstandiges Deuterium verteilt sich an Raney-Nickel auf samtl…

Cyclecondensation of 3-amino-1,2,4-triazole with substituted methyl cinnamates

1999

The reaction of 3-amino-1,2,4-triazole (1) with substituted methyl cinnamates 2a-h leads selectively to the formation of 7-aryl-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones 3a-h. The structure eluci dation of the products is based on ir, 1H and 13C nmr measurements and X-ray diffraction.

Ring-expansion of 5-methylene-thiazolidine-2-thione with hydrazine

2009

Mononuclear heterocyclic rearrangements 5. Kinetic Investigation of the behaviour of (e)- and (z)-phenylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadia…

1980

The kinetic behaviour of the geometrical isomers I-E and I-Z of the title compound in the presence of piperidine in benzene has been investigated. The kinetic results suggest that I-Z rearranges directly into 2,5-diphenyl-4-benzoylamino-1,2,3-triazole (II), whereas I-E probably rearranges only through the intermediate I-Z formed by isomerization. All the reactions studied are piperidine-catalyzed.