Oxadiazole

Last updated July 23, 2019

Oxadiazoles are a class of heterocyclic aromatic chemical compound of the azole family; with the molecular formula C₂H₂N₂O. There are four isomers of oxadiazole:

Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom as part of the ring. Their names originate from the Hantzsch–Widman nomenclature. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs with fewer. One, and only one, lone pair of electrons from each heteroatom in the ring is part of the aromatic bonding in an azole. Names of azoles maintain the prefix upon reduction. The numbering of ring atoms in azoles starts with the heteroatom that is not part of a double bond, and then proceeds towards the other heteroatom.

In chemistry, isomers are ions or molecules with identical formulas but distinct structures. Isomers do not necessarily share similar properties. Two main forms of isomerism are structural isomerism and stereoisomerism.

1,2,3-oxadiazole
1,2,4-oxadiazole
1,2,5-oxadiazole
(furazan)
1,3,4-oxadiazole

Furazan, or 1,2,5-oxadiazole, is a heterocyclic aromatic organic compound consisting of a five-atom ring containing 1 oxygen and 2 nitrogen atoms. The furazan ring system is also found in the steroid furazabol. Furazan and its derivatives are obtained from the oxime derivatives of 1,2-diketones.

1,3,4-Oxadiazole is a nitrogen and oxygen containing heterocycle, and one of the four isomers of oxadiazole.

1,2,4-Oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole are all known and appear in a variety of pharmaceutical drugs including raltegravir, butalamine, fasiplon, oxolamine, and pleconaril. The 1,2,3-isomer is unstable and ring-opens to form the diazo ketone tautomer;^[1] however, it does exist within the unusual sydnone motif.

Raltegravir (RAL), sold under the brand name Isentress, is an antiretroviral medication used, together with other medication, to treat HIV/AIDS. It may also be used, as part of post exposure prophylaxis, to prevent HIV infection following potential exposure. It is taken by mouth.

Butalamine is a vasodilator.

Fasiplon is a nonbenzodiazepine anxiolytic drug from the imidazopyrimidine family of drugs.

In 2018, a compound called bis(1,2,4-oxadiazole)bis(methylene) dinitrate which might have a 1.5 times the power of TNT was developed at the United States Army Research Laboratory (ARL) working with the Los Alamos National Laboratory.^[2]

Bis-oxadiazole, or more formally known as bis(1,2,4-oxadiazole)bis(methylene) dinitrate, is a nitrated heterocyclic compound of the oxadiazole family.

Trinitrotoluene (; TNT), or more specifically 2,4,6-Trinitrotoluene, is a chemical compound with the formula C₆H₂(NO₂)₃CH₃. This yellow solid is sometimes used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard measure of bombs and the power of explosives. In chemistry, TNT is used to generate charge transfer salts.

The Army Research Laboratory (ARL) is the U.S. Army's corporate research laboratory. ARL is headquartered at the Adelphi Laboratory Center (ALC) in Adelphi, Maryland. Its largest single site is at Aberdeen Proving Ground, Maryland. Other major ARL locations include Research Triangle Park, North Carolina, White Sands Missile Range, New Mexico, Orlando, Florida, and NASA's Glenn Research Center, Ohio and Langley Research Center, Virginia.

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An aromatic hydrocarbon or arene is a hydrocarbon with sigma bonds and delocalized pi electrons between carbon atoms forming a circle. In contrast, aliphatic hydrocarbons lack this delocalization. The term "aromatic" was assigned before the physical mechanism determining aromaticity was discovered; the term was coined as such simply because many of the compounds have a sweet or pleasant odour. The configuration of six carbon atoms in aromatic compounds is known as a benzene ring, after the simplest possible such hydrocarbon, benzene. Aromatic hydrocarbons can be monocyclic (MAH) or polycyclic (PAH).

Pyrazolopyrimidines are a series of isomeric heterocyclic chemical compounds with the molecular formula C₆H₅N₃. They form the central core of a variety of more complex chemical compounds including some pharmaceuticals and pesticides.

Benzoxazole is an aromatic organic compound with a molecular formula C₇H₅NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important.

Cyclic compound Molecule with a ring of bonded atoms

A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic, in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane, or HMDS) is an organosilicon compound with the molecular formula [(CH₃)₃Si]₂NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry.

1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C₄H₄O₂. It is an isomeric form of 1,4-dioxin (or p-dioxin).

Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp²-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated.

2,3-Dihydrothiophene is a heterocyclic compound and an organosulfur compound with the formula SC₄H₆. It is isomeric with the more symmetrical 2,5-dihydrothiophene. Both isomers of dihydrothiophene are colorless liquids with a thioether-like odor. In terms of their reactivity, both isomers exhibit characteristics of alkenes and thioethers, undergoing addition reactions at carbon and oxidation at sulfur. In contrast, thiophene engages in neither reaction.

Dihydrothiophene pair of isomeric chemical compounds

Dihydrothiophenes are heterocyclic organosulfur compounds. Two isomers are possible for the parent C₄H₆S:

2,5-Bis(hydroxymethyl)furan chemical compound

2,5-Bis(hydroxymethyl)furan (BHMF) is a heterocyclic organic compound, and is a derivative of a broader class of compounds known as furans. It is produced from cellulose and has received attention as a biofeedstock. It is a white solid, although commercial samples can appear yellowish or tan.

3-Bromofuran is a liquid having a boiling point similar to that of water (102.5-102.6 °C), but with density significantly higher

6-(2-Aminopropyl)indole is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czech Republic in July 2016.

Diazanaphthalenes are a class of aromatic heterocyclic chemical compounds that have the formula C₈H₆N₂. They consist of a naphthalene double ring in which two of the carbon atoms have been replaced with nitrogen atoms. There are ten positional isomers, which differ by the locations of the nitrogen atoms.

Thiadiazoles aromatic, heterocyclic compound having five-membered aromatic ring with two nitrogen and one sulfur heteroatoms

In chemistry thiadiazoles are a sub-family of azole compounds. Structurally they are five-membered heterocyclic compounds containing two nitrogen and a sulfur atoms, and two double bonds, to give an aromatic ring; with the name thiadiazole originating from the Hantzsch–Widman nomenclature. Four possible structures exist depending on the relative positions of the heteroatoms; these forms do not interconvert and hence are structural isomers and not tautomers. The compounds themselves are rarely synthesized and possess no particular application, however compounds bearing them as a structural motif are fairly common in pharmacology.

Cyclohexanehexathione is a cyclic covalent compound consisting of a six-carbon ring with a sulfur bonded to each. It has been synthesized by neutralization of its monoanion (C₆S₆^–) in a mass spectrometer. This compound is the thioketone analog of cyclohexanehexone; that oxygen variant is expected to be substantially less stable. Synthesis of C₆S₆ by photolysis or pyrolysis to extrude three equivalents of carbon monoxide from a precursor containing adjacent pairs of sulfurs as cyclic dithiocarbonate units gave what is more likely a different valence isomer, as various dithiete-containing structures are predicted to be more stable than the hexathione form.

References

↑ John A. Joule; Keith Mills (28 May 2013). Heterocyclic Chemistry. John Wiley & Sons. p. 842. ISBN 1-118-68164-9.
↑ "Double oxadiazole could replace TNT". c&en. 5 June 2018.

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[JouleMills2013-1] John A. Joule; Keith Mills (28 May 2013). Heterocyclic Chemistry. John Wiley & Sons. p. 842. ISBN 1-118-68164-9.

[2] "Double oxadiazole could replace TNT". c&en. 5 June 2018.