Heterocyclic compound: Difference between revisions

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role in modern medicinal chemistry
 
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{{Use dmy dates|date=July 2022}}
{{Use dmy dates|date=July 2022}}


[[File:Heterocycle compounds.jpg|thumb|right|class=skin-invert|280px|Structures and names of common heterocyclic compounds]]
[[File:Heterocycle compounds.jpg|thumb|right|class=skin-invert-image|upright=1.2|Structures and names of common heterocyclic compounds]]
[[Image:Pyridine.svg|thumb|class=skin-invert|right|125px|[[Pyridine]], a heterocyclic compound]]
[[Image:Pyridine.svg|thumb|class=skin-invert-image|right|upright=0.6|[[Pyridine]], a heterocyclic compound]]


A '''heterocyclic compound''' or '''ring structure''' is a [[cyclic compound]] that has atoms of at least two different [[chemical element|elements]] as members of its ring(s).<ref>[[IUPAC Gold Book]] [http://goldbook.iupac.org/H02798.html ''heterocyclic compounds'']</ref> '''Heterocyclic organic chemistry''' is the branch of [[organic chemistry]] dealing with the synthesis, properties, and applications of '''organic heterocycles'''.<ref name=Gilchrist/>
A '''heterocyclic compound''' or '''ring structure''' is a hydrocarbon-based [[cyclic compound]] that contains at least one [[heteroatom]] as member(s) of its ring(s).<ref>[[IUPAC Gold Book]] [http://goldbook.iupac.org/H02798.html ''heterocyclic compounds'']</ref> '''Heterocyclic organic chemistry''' is the branch of [[organic chemistry]] dealing with the synthesis, properties, and applications of '''organic heterocycles'''.<ref name=Gilchrist/>


Examples of heterocyclic compounds include all of the [[nucleic acids]], the majority of drugs, most [[biomass]] ([[cellulose]] and related materials), and many natural and synthetic dyes.  More than half of known compounds are heterocycles.<ref name=Rees>{{cite journal |doi=10.1002/jhet.5570290306|title=Polysulfur-Nitrogen Heterocyclic Chemistry|year=1992|last1=Rees|first1=Charles W.|journal=Journal of Heterocyclic Chemistry|volume=29|issue=3|pages=639–651}}</ref>  59% of US [[FDA]]-approved drugs contain [[nitrogen]] heterocycles.<ref>{{cite journal|author=Edon Vitaku, David T. Smith, Jon T. Njardarson|title=Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals|journal=J. Med. Chem.|volume=57|year=2014|issue=24|pages=10257–10274|doi=10.1021/jm501100b|pmid=25255204}}</ref>
Examples of heterocyclic compounds include all of the [[nucleic acids]], the majority of drugs, most [[biomass]] ([[cellulose]] and related materials), and many natural and synthetic dyes.  More than half of known compounds are heterocycles.<ref name=Rees>{{cite journal |doi=10.1002/jhet.5570290306|title=Polysulfur-Nitrogen Heterocyclic Chemistry|year=1992|last1=Rees|first1=Charles W.|journal=Journal of Heterocyclic Chemistry|volume=29|issue=3|pages=639–651}}</ref>  59% of US [[FDA]]-approved drugs contain [[nitrogen]] heterocycles.<ref>{{cite journal|author=Edon Vitaku, David T. Smith, Jon T. Njardarson|title=Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals|journal=J. Med. Chem.|volume=57|year=2014|issue=24|pages=10257–10274|doi=10.1021/jm501100b|pmid=25255204}}</ref>
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| [[Oxirane]]<br>([[ethylene oxide]], [[epoxide]]s)
| [[Oxirane]]<br>([[ethylene oxide]], [[epoxide]]s)
| [[Oxirene]]
| [[Oxirene]]
|-
| Silicon
| [[Silirane]]
| [[Silirene]]
|-
|-
| Phosphorus
| Phosphorus
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| 2 × Oxygen
| 2 × Oxygen
| [[Dioxirane]] (highly unstable)
| [[Dioxirane]] (highly unstable)
|
| - - - - - -
|-
|-
| 2 × Sulfur
| 2 × Sulfur
| [[Dithiirane]] (highly unstable)
| [[Dithiirane]] (highly unstable)
|
| - - - - - -
|}
|}


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| [[Oxetane]]
| [[Oxetane]]
| [[Oxete]]
| [[Oxete]]
|-
| Silicon
| [[Siletane]]
| [[Silete]]
|-
|-
| Phosphorus
| Phosphorus
Line 143: Line 151:
! Saturated
! Saturated
! Unsaturated
! Unsaturated
|-
| [[Antimony]]
| [[Stibolane]]
| [[Stibole]]
|-
| [[Arsenic]]
| [[Arsolane]]
| [[Arsole]]
|-
| [[Bismuth]]
| [[Bismolane]]
| [[Bismole]]
|-
|-
| [[Boron]]
| [[Boron]]
| [[Borolane]]
| [[Borolane]]
| [[Borole]]
| [[Borole]]
|-
| [[Germanium]]
| [[Germolane]]
| [[Germole]]
|-
|-
| [[Nitrogen]]
| [[Nitrogen]]
Line 171: Line 163:
| [[Oxolane]]
| [[Oxolane]]
| ''[[Furan]]''<br>([[Oxole]] not used)
| ''[[Furan]]''<br>([[Oxole]] not used)
|-
| [[Silicon]]
| [[Silolane]]
| [[Silole]]
|-
|-
| [[Phosphorus]]
| [[Phosphorus]]
| [[Phospholane]]
| [[Phospholane]]
| [[Phosphole]]
| [[Phosphole]]
|-
| [[Sulfur]]
| [[Thiolane]]
| ''[[Thiophene]]''<br>([[Thiole]] not used)
|-
| [[Germanium]]
| [[Germolane]]
| [[Germole]]
|-
| [[Arsenic]]
| [[Arsolane]]
| [[Arsole]]
|-
|-
| [[Selenium]]
| [[Selenium]]
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| [[Selenophene]]
| [[Selenophene]]
|-
|-
| [[Silicon]]
| [[Tin]]
| [[Silolane]]
| [[Stannolane]]
| [[Silole]]
| [[Stannole]]
|-
|-
| [[Sulfur]]
| [[Antimony]]
| [[Thiolane]]
| [[Stibolane]]
| ''[[Thiophene]]''<br>([[Thiole]] not used)
| [[Stibole]]
|-
|-
| [[Tellurium]]
| [[Tellurium]]
Line 192: Line 200:
| [[Tellurophene]]
| [[Tellurophene]]
|-
|-
| [[Tin]]
| [[Lead]]
| [[Stannolane]]
| [[Plumbolane]]
| [[Stannole]]
| [[Plumbole]]
|-
| [[Bismuth]]
| [[Bismolane]]
| [[Bismole]]
|-
|-
! colspan="3" | Five-membered rings with two heteroatoms
! colspan="3" | Five-membered rings with two heteroatoms
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| [[Dithiole]]
| [[Dithiole]]
|-
|-
! colspan="3" | Five-membered rings with three heteroatoms
! colspan="2" | Five-membered rings with three heteroatoms
|-
|-
! Heteroatoms
! Heteroatoms
! Saturated
! Unsaturated
! Unsaturated
|-
|-
| 3 × Nitrogen
| 3 × Nitrogen
|
| [[Triazole]]
| [[Triazole]]
|-
|-
| 2 Nitrogen + Oxygen
| 2 Nitrogen + Oxygen
|
| [[Oxadiazole]]
| [[Oxadiazole]]
|-
|-
| 2 Nitrogen + Sulfur
| 2 Nitrogen + Sulfur
|
| [[Thiadiazole]]
| [[Thiadiazole]]
|-
|-
| Nitrogen + 2 Oxygen
| Nitrogen + 2 Oxygen
|
| [[Dioxazole]]
| [[Dioxazole]]
|-
|-
| Nitrogen + 2 Sulfur
| Nitrogen + 2 Sulfur
|
| [[Dithiazole]]
| [[Dithiazole]]
|-
|-
! colspan="3" | Five-membered rings with four heteroatoms
! colspan="2" | Five-membered rings with four heteroatoms
|-
|-
! Heteroatoms
! Heteroatoms
! Saturated
! Unsaturated
! Unsaturated
|-
|-
| 4 × Nitrogen
| 4 × Nitrogen
|
| [[Tetrazole]]
| [[Tetrazole]]
|-
|-
| 3 Nitrogen + Oxygen
| 3 Nitrogen + Oxygen
|
| Oxatriazole
| [[Oxatriazole]]
|-
|-
| 3 Nitrogen + Sulfur
| 3 Nitrogen + Sulfur
|
| Thiatriazole
| [[Thiatriazole]]
|-
|-
! colspan="3" | Five-membered rings with five heteroatoms
! colspan="2" | Five-membered rings with five heteroatoms
|-
|-
! Heteroatoms
! Heteroatoms
! Saturated
! Unsaturated
! Unsaturated
|-
|-
| 5 × Nitrogen
| 5 × Nitrogen
|
| [[Pentazole]]
| [[Pentazole]]
|-
|-
| 4 Nitrogen + Oxygen
| 4 Nitrogen + Oxygen
|
| Oxatetrazole
| Oxatetrazole
|-
|-
| 4 Nitrogen + Sulfur
| 4 Nitrogen + Sulfur
|
| Thiatetrazole
| Thiatetrazole
|}
|}
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! Unsaturated
! Unsaturated
! Ions
! Ions
|-
| [[Antimony]]
| [[Stibinane]]
| [[Stibinine]]
| [[Stibatabenzene]] cation
|-
| [[Arsenic]]
| [[Arsinane]]
| [[Arsinine]]
| [[Arsatabenzene]] cation
|-
| [[Bismuth]]
| [[Bisminane]]
| [[Bismine]]
| [[Bismatabenzene]] cation
|-
|-
| [[Boron]]
| [[Boron]]
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| [[Borinine]]
| [[Borinine]]
| [[Boratabenzene]] anion
| [[Boratabenzene]] anion
|-
| [[Germanium]]
| [[Germinane]]
| [[Germine]]
|
|-
|-
| [[Nitrogen]]
| [[Nitrogen]]
Line 335: Line 313:
| ''[[Pyran]]''<br>([[Oxine]] not used)
| ''[[Pyran]]''<br>([[Oxine]] not used)
| [[Pyrylium]] cation
| [[Pyrylium]] cation
|-
| [[Silicon]]
| [[Silinane]]
| [[Siline]]
| - - - - - -
|-
|-
| [[Phosphorus]]
| [[Phosphorus]]
Line 340: Line 323:
| [[Phosphinine]]
| [[Phosphinine]]
| [[Phosphininium]] cation<ref name="C5R5PH+">{{cite journal |last1=Fischer |first1=Lukas |last2=Wossidlo |first2=Friedrich |last3=Frost |first3=Daniel |last4=Coles |first4=Nathan T. |last5=Steinhauer |first5=Simon |last6=Riedel |first6=Sebastian |last7=Müller |first7=Christian |date=6 August 2021 |orig-date=19th July 2021 |title=One-step methylation of aromatic phosphorus heterocycles: synthesis and crystallographic characterization of a 1-methyl-phosphininium salt |journal=Chemical Communications |volume= 57|issue=2021, '''57''' |publisher= Royal Society of Chemistry |pages=9522–9525 |doi=10.1039/D1CC03892C  |doi-access=free |pmid=34546255 }}</ref>
| [[Phosphininium]] cation<ref name="C5R5PH+">{{cite journal |last1=Fischer |first1=Lukas |last2=Wossidlo |first2=Friedrich |last3=Frost |first3=Daniel |last4=Coles |first4=Nathan T. |last5=Steinhauer |first5=Simon |last6=Riedel |first6=Sebastian |last7=Müller |first7=Christian |date=6 August 2021 |orig-date=19th July 2021 |title=One-step methylation of aromatic phosphorus heterocycles: synthesis and crystallographic characterization of a 1-methyl-phosphininium salt |journal=Chemical Communications |volume= 57|issue=2021, '''57''' |publisher= Royal Society of Chemistry |pages=9522–9525 |doi=10.1039/D1CC03892C  |doi-access=free |pmid=34546255 }}</ref>
|-
| [[Sulfur]]
| [[Thiane]]
| ''[[Thiopyran]]''<br>([[Thiine]] not used)
| [[Thiopyrylium]] cation
|-
| [[Germanium]]
| [[Germinane]]
| [[Germine]]
| - - - - - -
|-
| [[Arsenic]]
| [[Arsinane]]
| [[Arsinine]]
| [[Arsatabenzene]] cation
|-
|-
| [[Selenium]]
| [[Selenium]]
Line 346: Line 344:
| [[Selenopyrylium]] cation
| [[Selenopyrylium]] cation
|-
|-
| [[Silicon]]
| [[Tin]]
| [[Silinane]]
| [[Stanninane]]
| [[Siline]]
| [[Stannine]]
|
| - - - - - -
|-
|-
| [[Sulfur]]
| [[Antimony]]
| [[Thiane]]
| [[Stibinane]]
| ''[[Thiopyran]]''<br>([[Thiine]] not used)
| [[Stibinine]]
| [[Thiopyrylium]] cation
| [[Stibatabenzene]] cation
|-
|-
| [[Tellurium]]
| [[Tellurium]]
Line 361: Line 359:
| [[Telluropyrylium]] cation
| [[Telluropyrylium]] cation
|-
|-
| [[Tin]]
| [[Lead]]
| [[Stanninane]]
| [[Plumbinane]]
| [[Stannine]]
| [[Plumbine]]
|
| - - - - - -
|-
| [[Bismuth]]
| [[Bisminane]]
| [[Bismine]]
| [[Bismatabenzene]] cation
|-
|-
! colspan="3" | Six-membered rings with two heteroatoms
! colspan="3" | Six-membered rings with two heteroatoms
Line 389: Line 392:
|-
|-
| 2 × Oxygen
| 2 × Oxygen
| [[Dioxane]]
| [[Dioxane (compounds)|Dioxane]]
| [[Dioxin]]
| [[Dioxin]]
|-
|-
Line 414: Line 417:
| [[Trithiin]]
| [[Trithiin]]
|-
|-
! colspan="3" | Six-membered rings with four heteroatoms
! colspan="2" | Six-membered rings with four heteroatoms
|-
|-
! Heteroatoms
! Heteroatoms
! Saturated
! Unsaturated
! Unsaturated
|-
|-
| 4 × Nitrogen
| 4 × Nitrogen
|
| [[Tetrazine]]
| [[Tetrazine]]
|-
|-
| 2 Nitrogen + 2 Boron
| 2 Nitrogen + 2 Boron
|
| [[Carborazine]]
| [[Carborazine]]
|}
|}
Line 455: Line 455:
| [[Oxepane]]
| [[Oxepane]]
| [[Oxepine]]
| [[Oxepine]]
|-
| Silicon
| [[Silepane]]
| [[Silepine]]
|-
|-
| Phosphorus
| Phosphorus
Line 526: Line 530:


== Images of rings with one heteroatom ==
== Images of rings with one heteroatom ==
{| class="wikitable"
{| class="wikitable skin-invert-image"
|-
|-
!  colspan="1" | || colspan="3" | Saturated || colspan="3" | Unsaturated
!  colspan="1" | || colspan="3" | Saturated || colspan="3" | Unsaturated
Line 582: Line 586:
== Uses ==
== Uses ==
Heterocyclic compounds are pervasive in many areas of life sciences and technology.<ref name=Gilchrist>Thomas L. Gilchrist "Heterocyclic Chemistry" 3rd ed. Addison Wesley: Essex, England,
Heterocyclic compounds are pervasive in many areas of life sciences and technology.<ref name=Gilchrist>Thomas L. Gilchrist "Heterocyclic Chemistry" 3rd ed. Addison Wesley: Essex, England,
1997. 414 pp. {{ISBN|0-582-27843-0}}.</ref>  Many drugs are heterocyclic compounds.<ref>{{Cite web|url=http://www.ipexl.com/share/f593e64bc3679cb669d02c007efdca17|title=IPEXL.com Multilingual Patent Search, Patent Ranking|website=www.ipexl.com|access-date=8 September 2010|archive-date=24 September 2015|archive-url=https://web.archive.org/web/20150924035914/http://www.ipexl.com/share/f593e64bc3679cb669d02c007efdca17|url-status=dead}}</ref> Among the modifications to the family of antitumor compounds, heterocyclic organic compounds have been extensively applied by many groups in order to modify the reactivity profile. Pyrrole, pyrimidine, indole, quinoline and purine are few classes of heterocycles which showed interesting cytotoxicity profiles, which can be highly beneficial when developing cancer drugs. <ref>{{Cite journal |last1=Kidwai |first1=M. |last2=Venktaramanan |first2=R. |last3=Mohan |first3=R. |last4=Sapra |first4=P. |date=2002-06-01 |title=Cancer Chemotherapy and Heterocyclic Compounds |url=https://www.eurekaselect.com/article/9781 |journal=Current Medicinal Chemistry |language=en |volume=9 |issue=12 |pages=1209–1228 |doi=10.2174/0929867023370059 |pmid=12052173 |issn=0929-8673 |archive-url=http://web.archive.org/web/20240620060157/https://www.eurekaselect.com/article/9781 |archive-date=2024-06-20|url-access=subscription }}</ref>
1997. 414 pp. {{ISBN|0-582-27843-0}}.</ref>  Many drugs are heterocyclic compounds.<ref>{{Cite web|url=http://www.ipexl.com/share/f593e64bc3679cb669d02c007efdca17|title=IPEXL.com Multilingual Patent Search, Patent Ranking|website=www.ipexl.com|access-date=8 September 2010|archive-date=24 September 2015|archive-url=https://web.archive.org/web/20150924035914/http://www.ipexl.com/share/f593e64bc3679cb669d02c007efdca17|url-status=dead}}</ref> Among the modifications to the family of antitumor compounds, heterocyclic organic compounds have been extensively applied by many groups in order to modify the reactivity profile. Pyrrole, pyrimidine, indole, quinoline and purine are few classes of heterocycles which showed interesting cytotoxicity profiles, which can be highly beneficial when developing cancer drugs.<ref>{{Cite journal |last1=Kidwai |first1=M. |last2=Venktaramanan |first2=R. |last3=Mohan |first3=R. |last4=Sapra |first4=P. |date=2002-06-01 |title=Cancer Chemotherapy and Heterocyclic Compounds |url=https://www.eurekaselect.com/article/9781 |journal=Current Medicinal Chemistry |language=en |volume=9 |issue=12 |pages=1209–1228 |doi=10.2174/0929867023370059 |pmid=12052173 |issn=0929-8673 |archive-url=https://web.archive.org/web/20240620060157/https://www.eurekaselect.com/article/9781 |archive-date=2024-06-20|url-access=subscription }}</ref> Heterocyclic compounds play a central role in modern medicinal chemistry, with a large majority of newly approved drugs, containing at least one heterocyclic ring particularly nitrogen-containing systems. Their prevalence is attributed to their ability to modulate physicochemical properties such as solubility, lipophilicity, and binding affinity to biological targets<ref>{{Cite web |title=Индол: химия, свойства, получение и применение |url=https://indol-info.ru/ |access-date=2026-04-16 |website=indol-info.ru}}</ref>.


==See also==
==See also==
Line 594: Line 598:
{{wikiquote}}
{{wikiquote}}
* [http://www.chem.qmul.ac.uk/iupac/hetero/HW.html Hantzsch-Widman nomenclature, IUPAC]
* [http://www.chem.qmul.ac.uk/iupac/hetero/HW.html Hantzsch-Widman nomenclature, IUPAC]
* [http://www.cancer.gov/cancertopics/factsheet/Risk/heterocyclic-amines Heterocyclic amines in cooked meat, US CDC]
* [https://www.cancer.gov/cancertopics/factsheet/Risk/heterocyclic-amines Heterocyclic amines in cooked meat, US CDC]
* [http://www.cancer.org/docroot/PED/content/PED_1_3x_Known_and_Probable_Carcinogens.asp List of known and probable carcinogens, American Cancer Society] {{Webarchive|url=https://web.archive.org/web/20031213030702/http://www.cancer.org/docroot/PED/content/PED_1_3x_Known_and_Probable_Carcinogens.asp |date=13 December 2003 }}
* [http://www.cancer.org/docroot/PED/content/PED_1_3x_Known_and_Probable_Carcinogens.asp List of known and probable carcinogens, American Cancer Society] {{Webarchive|url=https://web.archive.org/web/20031213030702/http://www.cancer.org/docroot/PED/content/PED_1_3x_Known_and_Probable_Carcinogens.asp |date=13 December 2003 }}
* [http://www.scorecard.org/chemical-groups/one-list.tcl?short_list_name=p65 List of known carcinogens by the State of California], [[Proposition 65]] (more comprehensive)
* [http://www.scorecard.org/chemical-groups/one-list.tcl?short_list_name=p65 List of known carcinogens by the State of California], [[Proposition 65]] (more comprehensive)

Latest revision as of 14:07, 16 April 2026

For other uses of "ring structure", see Ring structure.
"Heterocycles" redirects here. For the journal, see Heterocycles (journal).

File:Heterocycle compounds.jpg
Structures and names of common heterocyclic compounds
File:Pyridine.svg
Pyridine, a heterocyclic compound

A heterocyclic compound or ring structure is a hydrocarbon-based cyclic compound that contains at least one heteroatom as member(s) of its ring(s).[1] Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles.[2]

Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles.[3] 59% of US FDA-approved drugs contain nitrogen heterocycles.[4]

Classification

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), hexachlorophosphazene (P3N3 ring), and trithiazyl trichloride (S3N3 ring). 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]

Notes on lists

  • "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.

3-membered rings

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

Three-membered rings with one heteroatom
Heteroatom Saturated Unsaturated
Boron Borirane Borirene
Nitrogen Aziridine Azirine
Oxygen Oxirane
(ethylene oxide, epoxides) 		Oxirene
Silicon Silirane Silirene
Phosphorus Phosphirane Phosphirene
Sulfur Thiirane
(ethylene sulfide, episulfides) 		Thiirene
Three-membered rings with two heteroatoms
Heteroatoms Saturated Unsaturated
2 × Nitrogen Diaziridine Diazirine
Nitrogen + Oxygen Oxaziridine Oxazirine
Nitrogen + Sulfur Thiaziridine Thiazirine
2 × Oxygen Dioxirane (highly unstable) - - - - - -
2 × Sulfur Dithiirane (highly unstable) - - - - - -

4-membered rings

Four-membered rings with one heteroatom
Heteroatom Saturated Unsaturated
Boron Boretane Borete
Nitrogen Azetidine Azete
Oxygen Oxetane Oxete
Silicon Siletane Silete
Phosphorus Phosphetane Phosphete
Sulfur Thietane Thiete
Four-membered rings with two heteroatoms
Heteroatoms Saturated Unsaturated
2 × Nitrogen Diazetidine Diazete
2 × Oxygen Dioxetane Dioxete
2 × Sulfur Dithietane Dithiete

5-membered rings

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. Dithioles have two sulfur atoms.

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.

Five-membered rings with one heteroatom
Heteroatom Saturated Unsaturated
Boron Borolane Borole
Nitrogen Pyrrolidine
(Azolidine not used) 		Pyrrole
(Azole not used)
Pyrroline (partially unsaturated)
Oxygen Oxolane Furan
(Oxole not used)
Silicon Silolane Silole
Phosphorus Phospholane Phosphole
Sulfur Thiolane Thiophene
(Thiole not used)
Germanium Germolane Germole
Arsenic Arsolane Arsole
Selenium Selenolane Selenophene
Tin Stannolane Stannole
Antimony Stibolane Stibole
Tellurium Tellurolane Tellurophene
Lead Plumbolane Plumbole
Bismuth Bismolane Bismole
Five-membered rings with two heteroatoms
Heteroatoms Saturated Unsaturated (and partially unsaturated)
2 × Nitrogen Pyrazolidine
Imidazolidine 		Pyrazole (Pyrazoline)
Imidazole (Imidazoline)
Nitrogen + Oxygen Oxazolidine
Isoxazolidine 		Oxazole (Oxazoline)
Isoxazole (Isoxazoline)
Nitrogen + Sulfur Thiazolidine
Isothiazolidine 		Thiazole (Thiazoline)
Isothiazole (Isothiazoline)
Oxygen + Sulfur Oxathiolane
Isoxathiolane 		Oxathiole
Isoxathiole
2 × Oxygen Dioxolane Dioxole
2 × Sulfur Dithiolane Dithiole
Five-membered rings with three heteroatoms
Heteroatoms Unsaturated
3 × Nitrogen Triazole
2 Nitrogen + Oxygen Oxadiazole
2 Nitrogen + Sulfur Thiadiazole
Nitrogen + 2 Oxygen Dioxazole
Nitrogen + 2 Sulfur Dithiazole
Five-membered rings with four heteroatoms
Heteroatoms Unsaturated
4 × Nitrogen Tetrazole
3 Nitrogen + Oxygen Oxatriazole
3 Nitrogen + Sulfur Thiatriazole
Five-membered rings with five heteroatoms
Heteroatoms Unsaturated
5 × Nitrogen Pentazole
4 Nitrogen + Oxygen Oxatetrazole
4 Nitrogen + Sulfur Thiatetrazole

6-membered rings

The 6-membered ring compounds containing two heteroatoms, at least one of which is nitrogen, are collectively called the azines. Thiazines contain a sulfur and a nitrogen atom in the ring. Dithiines have two sulfur atoms.

Six-membered rings with one heteroatom
Heteroatom Saturated Unsaturated Ions
Boron Borinane Borinine Boratabenzene anion
Nitrogen Piperidine
(Azinane not used) 		Pyridine
(Azine not used) 		Pyridinium cation
Oxygen Oxane Pyran
(Oxine not used) 		Pyrylium cation
Silicon Silinane Siline - - - - - -
Phosphorus Phosphinane Phosphinine Phosphininium cation[7]
Sulfur Thiane Thiopyran
(Thiine not used) 		Thiopyrylium cation
Germanium Germinane Germine - - - - - -
Arsenic Arsinane Arsinine Arsatabenzene cation
Selenium Selenane Selenopyran Selenopyrylium cation
Tin Stanninane Stannine - - - - - -
Antimony Stibinane Stibinine Stibatabenzene cation
Tellurium Tellurane Telluropyran Telluropyrylium cation
Lead Plumbinane Plumbine - - - - - -
Bismuth Bisminane Bismine Bismatabenzene cation
Six-membered rings with two heteroatoms
Heteroatoms Saturated Unsaturated
2 × Nitrogen Piperazine Pyrazine
Pyrimidine
Pyridazine
Nitrogen + Oxygen Morpholine Oxazine
Nitrogen + Sulfur Thiomorpholine Thiazine
Oxygen + Sulfur Oxathiane Oxathiin
2 × Oxygen Dioxane Dioxin
2 × Sulfur Dithiane Dithiin
Six-membered rings with three heteroatoms
Heteroatoms Saturated Unsaturated
3 × Nitrogen Triazinane Triazine
3 × Oxygen Trioxane Trioxin
3 × Sulfur Trithiane Trithiin
Six-membered rings with four heteroatoms
Heteroatoms Unsaturated
4 × Nitrogen Tetrazine
2 Nitrogen + 2 Boron Carborazine

Six-membered rings with five heteroatoms
The hypothetical chemical compound with five nitrogen heteroatoms would be pentazine.

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.

7-membered rings

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.

Seven-membered rings with one heteroatom
Heteroatom Saturated Unsaturated
Boron Borepane Borepine
Nitrogen Azepane Azepine
Oxygen Oxepane Oxepine
Silicon Silepane Silepine
Phosphorus Phosphepane Phosphepine
Sulfur Thiepane Thiepine
Seven-membered rings with two heteroatoms
Heteroatoms Saturated Unsaturated
2 × Nitrogen Diazepane Diazepine
Nitrogen + Oxygen Oxazepane Oxazepine
Nitrogen + Sulfur Thiazepane Thiazepine

8-membered rings

Heteroatom Saturated Unsaturated
Nitrogen Azocane Azocine
Oxygen Oxocane Oxocine
Sulfur Thiocane Thiocine

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

9-membered rings

Heteroatom Saturated Unsaturated
Nitrogen Azonane Azonine
Oxygen Oxonane Oxonine
Sulfur Thionane Thionine

Images of rings with one heteroatom

Saturated Unsaturated
Heteroatom Nitrogen Oxygen Sulfur Nitrogen Oxygen Sulfur
3-atom ring Aziridine Oxirane Thiirane Azirine Oxirene Thiirene
Structure of aziridine Structure of oxirane Structure of thiirane Structure of azirine Structure of oxirene Structure of thiirene
4-atom ring Azetidine Oxetane Thietane Azete Oxete Thiete
Structure of acetidine Structure of oxetane Structure of thietane Structure of azete Structure of oxete Structure of thiete
5-atom ring Pyrrolidine Oxolane Thiolane Pyrrole Furan Thiophene
Structure of pyrrolidine Structure of oxolane Structure of thiolane Structure of pyrrole Structure of furan Structure of thiophene
6-atom ring Piperidine Oxane Thiane Pyridine Pyran Thiopyran
Structure of piperidine Structure of oxane Structure of thiane Structure of pyridine Structure of pyran Structure of thiopyran
7-atom ring Azepane Oxepane Thiepane Azepine Oxepine Thiepine
Structure of azepane Structure of oxepane Structure of thiepane Structure of azepine Structure of oxepine Structure of thiepine
8-atom ring Azocane Oxocane Thiocane Azocine Oxocine Thiocine
Structure of azocane Structure of oxocane Structure of thiocane Structure of azocine Structure of oxocine Structure of thiocine
9-atom ring Azonane Oxonane Thionane Azonine Oxonine Thionine
Structure of azonane Structure of oxonane Structure of thionane Structure of azonine Structure of oxonine Structure of thionine

Fused/condensed rings

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 derivative is quinoline or isoquinoline, and the class of analogues with two nitrogen atoms is known as the benzodiazines. For the azepine derivative, benzazepine is the preferred name. Likewise, the compounds with two benzene rings fused to the central heterocycle are carbazole, acridine, and dibenzoazepine. Heptazine is a tricyclic nitrogen-containing heterocyclic system derived by fusion of three triazine rings, and analog of the carbocycle phenalene.

History of heterocyclic chemistry

The history of heterocyclic chemistry began in the 1800s, in step with the development of organic chemistry. Some noteworthy developments:[8]

  • 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.

Uses

Heterocyclic compounds are pervasive in many areas of life sciences and technology.[2] Many drugs are heterocyclic compounds.[9] Among the modifications to the family of antitumor compounds, heterocyclic organic compounds have been extensively applied by many groups in order to modify the reactivity profile. Pyrrole, pyrimidine, indole, quinoline and purine are few classes of heterocycles which showed interesting cytotoxicity profiles, which can be highly beneficial when developing cancer drugs.[10] Heterocyclic compounds play a central role in modern medicinal chemistry, with a large majority of newly approved drugs, containing at least one heterocyclic ring particularly nitrogen-containing systems. Their prevalence is attributed to their ability to modulate physicochemical properties such as solubility, lipophilicity, and binding affinity to biological targets[11].

See also

References

  1. ↑ IUPAC Gold Book heterocyclic compounds
  2. ↑ 2.0 2.1 Thomas L. Gilchrist "Heterocyclic Chemistry" 3rd ed. Addison Wesley: Essex, England, 1997. 414 pp. ISBN 0-582-27843-0.
  3. ↑ Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.
  4. ↑ Edon Vitaku, David T. Smith, Jon T. Njardarson (2014). "Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals". J. Med. Chem. 57 (24): 10257–10274. doi:10.1021/jm501100b. PMID 25255204.CS1 maint: multiple names: authors list (link)
  5. ↑ Template:GoldBookRef
  6. ↑ Template:March6th
  7. ↑ Fischer, Lukas; Wossidlo, Friedrich; Frost, Daniel; Coles, Nathan T.; Steinhauer, Simon; Riedel, Sebastian; Müller, Christian (6 August 2021) [19th July 2021]. "One-step methylation of aromatic phosphorus heterocycles: synthesis and crystallographic characterization of a 1-methyl-phosphininium salt". Chemical Communications. Royal Society of Chemistry. 57 (2021, 57): 9522–9525. doi:10.1039/D1CC03892C. PMID 34546255.
  8. ↑ Campaigne, E. (1986). "Adrien Albert and the rationalization of heterocyclic chemistry". Journal of Chemical Education. 63 (10): 860. Bibcode:1986JChEd..63..860C. doi:10.1021/ed063p860.
  9. ↑ "IPEXL.com Multilingual Patent Search, Patent Ranking". www.ipexl.com. Archived from the original on 24 September 2015. Retrieved 8 September 2010.
  10. ↑ Kidwai, M.; Venktaramanan, R.; Mohan, R.; Sapra, P. (1 June 2002). "Cancer Chemotherapy and Heterocyclic Compounds". Current Medicinal Chemistry. 9 (12): 1209–1228. doi:10.2174/0929867023370059. ISSN 0929-8673. PMID 12052173. Archived from the original on 20 June 2024.
  11. ↑ "Индол: химия, свойства, получение и применение". indol-info.ru. Retrieved 16 April 2026.
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