2-Aminothiazole

Last updated
2-Aminothiazole
2-aminothiazool.png
2-Aminothiazole-3D-spacefill.png
Names
Preferred IUPAC name
1,3-Thiazol-2-amine
Other names
2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.284 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-511-6
KEGG
PubChem CID
UNII
  • InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) Yes check.svgY
    Key: RAIPHJJURHTUIC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
    Key: RAIPHJJURHTUIC-UHFFFAOYAZ
  • c1csc(n1)N
Properties
C3H4N2S
Molar mass 100.14 g·mol−1
AppearanceLight yellow crystals
Melting point 86 to 89 °C (187 to 192 °F; 359 to 362 K)
Boiling point 117 °C (243 °F; 390 K) (20 hPa)
100 g/L (20 °C)
-56.0·10−6 cm3/mol
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H319
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
600 °C (1,112 °F; 873 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism. [2]

Contents

2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride. [3]

2-Aminothiazoles

Like the parent, 2-aminothiazoles are often produced by the condensation of thiourea and an alpha-halo ketone. [4] [5] [6]

Hantsch Thiazole Synthesis HantzschThiazole-Synthesis.png
Hantsch Thiazole Synthesis

In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketone reacts with phosphorus pentasulfide.

Applications

Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in medicinal chemistry. Some examples are abafungin, acotiamide, amiphenazole, amthamine, avatrombopag, aztreonam, cefepime, cefixime, ceftizoxime, ceftiofur, ceftibuten, cefpirome, famotidine, meloxicam, and pramipexole. [7] [8]

Related Research Articles

<span class="mw-page-title-main">Hydrazone</span> Organic compounds - Hydrazones

Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Chalcone</span> Chemical compound

Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

Thiourea is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom ; however, the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the general structure R2N−C(=S)−NR2.

The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. Modified versions of which were subsequently refined and published in Organic Syntheses.

<span class="mw-page-title-main">Iminium</span> Polyatomic ion of the form >C=N< and charge +1

In organic chemistry, an iminium cation is a polyatomic ion with the general structure [R1R2C=NR3R4]+. They are common in synthetic chemistry and biology.

The Dakin–West reaction is a chemical reaction that transforms an amino-acid into a keto-amide using an acid anhydride and a base, typically pyridine. It is named for Henry Drysdale Dakin (1880–1952) and Randolph West (1890–1949). In 2016 Schreiner and coworkers reported the first asymmetric variant of this reaction employing short oligopeptides as catalysts.

<span class="mw-page-title-main">Cyanamide</span> Chemical compound featuring a nitrile group attached to an amino group

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).

In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. Named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978), the method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids.

The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with cyanide in the presence of ammonia. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used for the commercial production of racemic methionine from methional.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">Alkylimino-de-oxo-bisubstitution</span> Organic reaction of carbonyl compounds with amines to imines

In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. The reaction name is based on the IUPAC Nomenclature for Transformations. The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines water is lost in an elimination reaction to an imine. With aryl amines especially stable Schiff bases are formed.

α-Halo ketone

In organic chemistry, an α-halo ketone is a functional group consisting of a ketone group or more generally a carbonyl group with an α-halogen substituent. α-Halo ketones are alkylating agents. Prominent α-halo ketones include phenacyl bromide and chloroacetone.

<span class="mw-page-title-main">Thioureas</span> Organosulfur compounds with an >NC(=S)N< structure

In organic chemistry, thioureas are members of a family of organosulfur compounds with the formula S=C(NR2)2 and structure R2N−C(=S)−NR2. The parent member of this class of compounds is thiourea. Substituted thioureas are found in several commercial chemicals.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

The Cook–Heilbron thiazole synthesis highlights the formation of 5-aminothiazoles through the chemical reaction of α-aminonitriles or aminocyanoacetates with dithioacids, carbon disulphide, carbon oxysulfide, or isothiocyanates at room temperature and under mild or aqueous conditions. Variation of substituents at the 2nd and 4th position of the thiazole is introduced by selecting different combinations of starting reagents.

1-Naphthol, or α-naphthol, is a organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds.

<span class="mw-page-title-main">Indole</span> Chemical compound

Indole is an aromatic, heterocyclic, organic compound with the formula C8H7N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin.

<span class="mw-page-title-main">Pinacolborane</span> Chemical compound

Pinacolborane is the borane with the formula (CH3)4C2O2BH. Often pinacolborane is abbreviated HBpin. It features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. It features a reactive B-H functional group.

References

  1. "2-Aminothiazole". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2022.
  2. Dahlmanns, Simone M.; Müller-Gärtner, Hans-Wilhelm (2000). "Thyrotherapeutic Agents". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_039. ISBN   9783527303854.
  3. Erlenmeyer, H.; Herzfeld, L.; Prijs, B. (1955). "Zur Synthese von 2-Amino-thiazolderivaten". Helvetica Chimica Acta. 38 (5): 1291–1294. doi:10.1002/hlca.19550380529.
  4. J. R. Byers; J. B. Dickey (1939). "2-Amino-4-methylthiazole". Organic Syntheses . 19: 10. doi:10.15227/orgsyn.019.0010.
  5. Gómez, Antonio Bermejo; Ahlsten, Nanna; Platero-Prats, Ana E.; Martín-Matutejournal=Organic Syntheses, Belén (2014). "Synthesis of 4,5-Disubstituted 2-Aminothiazoles from α,β-Unsaturated Ketones: Preparation of 5-Benzyl-4-methyl-2-aminothiazolium Hydrochloride Salt". Organic Syntheses. 91: 185–200. doi: 10.15227/orgsyn.091.0185 .
  6. Alajarín, M.; Cabrera, J.; Pastor, A.; Sánchez-Andrada, P.; Bautista, D. (2006). "On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes". J. Org. Chem. 71 (14): 5328–5339. doi:10.1021/jo060664c. PMID   16808523.
  7. Das, Debasis; Sikdar, Papiya; Bairagi, Moumita (2016). "Recent Developments of 2-Aminothiazoles in Medicinal Chemistry". European Journal of Medicinal Chemistry. 109: 89–98. doi:10.1016/j.ejmech.2015.12.022. PMID   26771245.
  8. Wan, Yichao; Long, Jiabing; Gao, Han; Tang, Zilong (2021). "2-Aminothiazole: A privileged scaffold for the discovery of anti-cancer agents". European Journal of Medicinal Chemistry. 210. doi:10.1016/j.ejmech.2020.112953. PMID   33148490. S2CID   226258989.