Heterocyclic compound

The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinoline, benzothiophene, indole, and benzofuran, respectively. The fusion of two benzene rings gives rise to a third large family of organic compounds. Analogs of the previously mentioned heterocycles for this third family of compounds are acridine, dibenzothiophene, carbazole, and dibenzofuran, respectively.

Heterocyclic organic compounds can be usefully classified based on their electronic structure. The saturated organic heterocycles behave like the acyclic derivatives. Thus, piperidine and tetrahydrofuran are conventional amines and ethers, with modified steric profiles. Therefore, the study of organic heterocyclic chemistry focuses on organic unsaturated rings.

Inorganic rings

Some heterocycles contain no carbon. Examples are borazine (B₃N₃ ring), hexachlorophosphazenes (P₃N₃ rings), and tetrasulfur tetranitride S₄N₄. In comparison with organic heterocycles, which have numerous commercial applications, inorganic ring systems are mainly of theoretical interest. IUPAC recommends the Hantzsch-Widman nomenclature for naming heterocyclic compounds.^[5]

• "Heteroatoms" are atoms in the ring other than carbon atoms.
• Names in italics are retained by IUPAC and do not follow the Hantzsch-Widman nomenclature
• Some of the names refer to classes of compounds rather than individual compounds.
• Also no attempt is made to list isomers.

Although subject to ring strain, 3-membered a heterocyclic rings are well characterized.^[6]

Three-membered rings with one heteroatom

Three-membered rings with two heteroatoms

Four-membered rings with one heteroatom

Four-membered rings with two heteroatoms

Five-membered rings with one heteroatom

Five-membered rings with two heteroatoms

The 5-membered ring compounds containing two heteroatoms, at least one of which is nitrogen, are collectively called the azoles. Thiazoles and isothiazoles contain a sulfur and a nitrogen atom in the ring. Dithiolanes have two sulfur atoms.

Five-membered rings with at least three heteroatoms

A large group of 5-membered ring compounds with three or more heteroatoms also exists. One example is the class of dithiazoles, which contain two sulfur atoms and one nitrogen atom.

Six-membered rings with one heteroatom

Six-membered rings with two heteroatoms

Six-membered rings with three heteroatoms

Six-membered rings with four heteroatoms

Carborazine is a six-membered ring with two nitrogen heteroatoms and two boron heteroatom.

Six-membered rings with five heteroatoms

Six-membered rings with six heteroatoms

The hypothetical chemical compound with six nitrogen heteroatoms would be hexazine.

Borazine is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms.

In a 7-membered ring, the heteroatom must be able to provide an empty π-orbital (e.g. boron) for "normal" aromatic stabilization to be available; otherwise, homoaromaticity may be possible. Compounds with one heteroatom include:

Those with two heteroatoms include:

Borazocine is an eight-membered ring with four nitrogen heteroatoms and four boron heteroatoms.

Heterocyclic rings systems that are formally derived by fusion with other rings, either carbocyclic or heterocyclic, have a variety of common and systematic names. For example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides indole or isoindole depending on the orientation. The pyridine analog is quinoline or isoquinoline. For azepine, benzazepine is the preferred name. Likewise, the compounds with two benzene rings fused to the central heterocycle are carbazole, acridine, and dibenzoazepine. Thienothiophene are the fusion of two thiophene rings. Phosphaphenalenes are a tricyclic phosphorus-containing heterocyclic system derived from the carbocycle phenalene.

The history of heterocyclic chemistry began in the 1800s, in step with the development of organic chemistry. Some noteworthy developments:^[10]

• 1818: Brugnatelli makes alloxan from uric acid
• 1832: Dobereiner produces furfural (a furan) by treating starch with sulfuric acid
• 1834: Runge obtains pyrrole ("fiery oil") by dry distillation of bones
• 1906: Friedlander synthesizes indigo dye, allowing synthetic chemistry to displace a large agricultural industry
• 1936: Treibs isolates chlorophyll derivatives from crude oil, explaining the biological origin of petroleum.
• 1951: Chargaff's rules are described, highlighting the role of heterocyclic compounds (purines and pyrimidines) in the genetic code.

Heterocyclic compounds are pervasive in many areas of life sciences and technology.^[2] Many drugs are heterocyclic compounds.^[11]

• Spiroketals

Wikimedia Commons has media related to heterocyclic compounds.

Wikiquote has quotations related to Heterocyclic compound.

• Hantzsch-Widman nomenclature, IUPAC
• Heterocyclic amines in cooked meat, US CDC
• List of known and probable carcinogens, American Cancer Society Archived 13 December 2003 at the Wayback Machine
• List of known carcinogens by the State of California, Proposition 65 (more comprehensive)