Acylhydrazine

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An example of an acylhydrazine. This compound has been called acetylhydrazide, acetohydrazide, or acetic acid hydrazide. Acetylhydrazine.svg
An example of an acylhydrazine. This compound has been called acetylhydrazide, acetohydrazide, or acetic acid hydrazide.

Acylhydrazines are a class of organic compounds and can be regarded as nitrogen derivatives of carboxylic acids having the general structure R-CO-NR1-NR2R3, where R1, R2 and R3 can be organic radicals or hydrogen. They are analogous to an amide, but the -OH portion of a carboxylic acid is replaced by hydrazine rather than ammonia (one less hydrogen at the point of attachment). Acylhydrazines are a type of hydrazides.

Organic compound Chemical compound that contains carbon (except for several compounds traditionally classified as inorganic compounds)

In chemistry, organic compounds are generally any chemical compounds that contain carbon. Due to carbon's ability to catenate, millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprises the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds, along with a handful of other exceptions, are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive.

In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction.

Carboxylic acid oxoacid having the structure RC(=O)OH, used as a suffix in systematic name formation to denote the –C(=O)OH group including its carbon atom

A carboxylic acid is an organic compound that contains a carboxyl group. The general formula of a carboxylic acid is R–COOH, with R referring to the rest of the molecule. Carboxylic acids occur widely. Important examples include the amino acids and acetic acid. Deprotonation of a carboxyl group gives a carboxylate anion.

Contents

Formic acid chemical compound

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid. The chemical formula is . The chemical composition is HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. The word "formic" comes from the Latin word for ant, formica, referring to its early isolation by the distillation of ant bodies. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

Acetic acid A colourless liquid organic compound found in vinegar

Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2). When undiluted, it is sometimes called glacial acetic acid. Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate and cellulose acetate. It is classified as a weak acid since it only partially dissociates in solution, but concentrated acetic acid is corrosive and can attack the skin.

Preparation

Carboxylic hydrazides can be prepared by reacting acyl halides with hydrazine (or correspondingly substituted hydrazines) or by reduction of N-nitroso carboxamides. [2]

Acyl halide any chemical compound having a halogen atom bonded to an acyl group

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

Hydrazine A colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N
2
H
4
. It is a simple pnictogen hydride, and is a colorless and flammable liquid with an ammonia-like odor.

Nitroso functional group having the structure –NO

Nitroso refers to a functional group in organic chemistry which has the NO group attached to an organic moiety. As such, various nitroso groups can be categorized as C-nitroso compounds (e.g., nitrosoalkanes; R−N=O), S-nitroso compounds (nitrosothiols; RS−N=O), N-nitroso compounds (e.g., nitrosamines, R1N(−R2)−N=O), and O-nitroso compounds (alkyl nitrites; RO−N=O).

Properties

Carboxylic hydrazides are stable, polar solids and partially pharmacologically active. [2]

Use

Acylhydrazines are intermediates in chemical syntheses, for example in the synthesis of nitrogen heterocycles and acyl azides. [3]

Heterocyclic compound cyclic chemical compound having as ring members atoms of at least two different elements

A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.

Acyl azide any organic azide in which an azide group is attached to a carboacyl group

Acyl azides are carboxylic acid derivatives with the general formula RCON3.

An applied example is a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate. [4] After 4 hours at 110 °C, the indole ring structure has been broken into (2-amino-5-fluoro-phenyl)-acetic acid hydrazide with reduction of the ketone at the 3-position. Subsequent annelation in strong acid creates the 1,3-dihydro-2-oxo indole structure required for the drug.

Sunitinib Cancer medication

Sunitinib is an oral, small-molecule, multi-targeted receptor tyrosine kinase (RTK) inhibitor that was approved by the FDA for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST) on January 26, 2006. Sunitinib was the first cancer drug simultaneously approved for two different indications.

Isatin chemical compound

Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.

Related Research Articles

Amide group of chemical substances

An amide, also known as an acid amide, is a compound with the functional group RnE(O)xNR′2. Most common are carboxamides, but many other important types of amides are known, including phosphoramides and sulfonamides. The term amide refers both to classes of compounds and to the functional group within those compounds.

Ester chemical compounds consisting of a carbonyl adjacent to an ether linkage

In chemistry, an ester − as opposed to an ether − is a chemical compound derived from an acid in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group. Usually, esters are derived from a carboxylic acid and an alcohol. Glycerides, which are fatty acid esters of glycerol, are important esters in biology, being one of the main classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties. Esters usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers. They are also one of the largest classes of synthetic lubricants on the commercial market.

Ketene any organic compound having a carbonyl group connected by a double bond to an alkylidene group

A ketene is an organic compound of the form R′R″C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refers to the specific compound ethenone H
2
C=C=O
, the simplest ketene.

Viscose is a term often used to represent the viscose fiber that is made from natural sources such as wood and agricultural products that are regenerated as cellulose fiber. The molecular structure of natural cellulose is preserved in the process. The many types and grades of viscose fibers can imitate the feel and texture of natural fibers such as silk, wool, cotton, and linen. The types that resemble silk are often called artificial silk.</ref> The fibre is used to make textiles for clothing and other purposes.

Acyl chloride any chemical compound having a chlorine atom bonded to a carboacyl group

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Imide class of chemical compounds

In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant toward hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides.

Acetyl chloride chemical compound

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless, corrosive, volatile liquid.

The Leimgruber–Batcho indole synthesis is a series of organic reactions that produce indoles from o-nitrotoluenes 1. The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine. The desired indole 3 is then formed in a second step by reductive cyclisation.

The Madelung synthesis is a chemical reaction that produces indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature.The Madelung synthesis was reported in 1912 by Walter Madelung, when he observed that 2-phenylindole was synthesized using N-benzoyl-o-toluidine and two equivalents of sodium ethoxide in a heated, airless, reaction. Common reaction conditions include use of sodium or potassium alkoxide as base in hexane or tetrahydrofuran solvents, at temperatures ranging between 200–400 °C. A hydrolysis step is also required in the synthesis. The Madelung synthesis is important because it is one of few known reactions that produce indoles from a base-catalyzed thermal cyclization of N-acyl-o-toluidines. The overall reaction for the Madelung synthesis follows.

Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Aryl sulfonic acids are used as detergents, dye, and drugs.

Curtius rearrangement chemical reaction

The Curtius rearrangement, first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate or urea derivative respectively. Several reviews have been published.

Hydrazide

Hydrazides in organic chemistry are a class of organic compounds sharing a common functional group characterized by hydrazine core in which at least one of the hydrogen atoms is replaced by a substituent that is an acyl group. The general structure for a hydrazide is E(=O)-NR-NR2, where the R's are frequently hydrogens. Hydrazides can be further classified by atom attached to the oxygen: carbohydrazides (R-C(=O)-NH-NH2), sulfonohydrazides (R-S(=O)2-NH-NH2) and phosphonic dihydrazides (R-P(=O)(-NH-NH2)2. The related hydrazines do not carry an acyl group. Some important members of this class are sulfonylhydrazides such as p-toluenesulfonylhydrazide which are useful reagents in organic chemistry such as in the Shapiro reaction and the Eschenmoser–Tanabe fragmentation. This reagent can be prepared by reaction of tosyl chloride with hydrazine.

Crotonic acid chemical compound

Crotonic acid ((2E)-but-2-enoic acid) or is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water. The cis-isomer of crotonic acid is called isocrotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to butyric acid.

Pyridazine chemical compound

Pyridazine is a heterocyclic organic compound with the molecular formula (CH)4N2. It contains a six-membered ring with two adjacent nitrogen atoms, and is aromatic. It is a colorless liquid with a boiling point of 208 °C. It is isomeric with two other (CH)4N2 rings, pyrimidine and pyrazine.

Aminolysis (/am·i·nol·y·sis/ amino meaning "contains NH2 group", and lysis meaning "to unbind") is any chemical compound reacts with a molecule of ammonia or an amine and causes a molecule to split into two parts, containing the addition of (or substitution by) an amino group —NH—. The subset of aminolysis reactions involving ammonia is known as ammonolysis.

Hydrazines organic derivatives of hydrazine of which protons have been replaced with one or more alkyl or aryl groups

Hydrazines (R2N-NR2) are a class of chemical compounds which have two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. Hydrazines can be considered as derivatives of the inorganic hydrazine (H2N-NH2), in which one or more hydrogen atoms have been replaced by hydrocarbon groups.

Sulfanilic acid Chemical compound

Sulfanilic acid is an off-white crystalline solid which finds application in quantitative analysis of nitrate and nitrite ions. The solid acid exists as a zwitterion, and has an unusually high melting point.

The alkylbenzenes are derivatives of benzene, in which one or more hydrogen atoms are replaced by alkyl groups of different sizes. They are a subset of the aromatic hydrocarbons. The simplest member is toluene, in which a hydrogen atom of the benzene was replaced by a methyl group.

References

  1. "ChemicalBook:2-(4-ethylphenoxy)acetylhydrazide".
  2. 1 2 Siegfried Hauptmann: Organische Chemie, 2. Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, S. 425, ISBN   3-342-00280-8.
  3. Siegfried Hauptmann: Organische Chemie, 2. Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, S. 426, ISBN   3-342-00280-8.
  4. "US patent 6573293". Archived from the original on 2012-09-06.