I 1887 Arthur Rudolf Hantzsch og JH Weber offentliggjort en af de første publikationer om nomenklatur af heterocykliske forbindelser . Et år senere offentliggjorde Oskar Widman en artikel, der uafhængigt foreslog en nomenklatur for heterocykliske stoffer baseret på de samme principper som dem, der blev beskrevet af Hantzsch. En syntese såvel som en udvidelse af disse metoder blev udført i 1940'erne. Denne nomenklatur blev vedtaget af IUPAC i 1957 og er siden blevet revideret og suppleret af en kommission af IUPAC.
Billedtekst:
Ved hver (X, Y), tabel med type heteroatom i kolonne og antal heteroatom i række.
I det særlige tilfælde af en ring (X, Y), der indeholder X heteroatomer af samme type, er denne ring ikke længere strengt taget en heterocyklus - den indeholder ikke længere et carbonatom - og i det tilfælde, hvor denne ring ikke længere indeholder ethvert hydrogenatom som i tetraazet eller hexaselenan, er det først og fremmest en allotrop af dette heteroatom (element).
cyclopropan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | aziridin (aziran) | phosphiran | arsirane | oxiran ( epoxy ) | thiiran ( episulfid ) | seleniran (episelenid) |
2 | diaziridin | diphosphiran | diarsiran | dioxiran | dithiirane | diseleniran |
3 | triaziridin | - | - | trioxiran | trithiirane | - |
cyclopropen
heteroatom | IKKE | P | Es | O | S | Se | B |
---|---|---|---|---|---|---|---|
1 | azirin (aziren) | phosphiren | arsirene | oxiren | thiirene | selenirene | borirene |
2 | diazirene | diphosphiren | diarsirene | - | - | - | - |
3 | - | - | - | - | - | - | - |
cyclobutan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azetidin (azetan) | phosphetan | arsetan | oxetan | thietane | selenetan |
2 | 1,2-diazetidin (diazetan) 1,3-diazetidin |
1,2-diphosphetan 1,3-diphosphetan |
1,3-diarsetan |
1,2-dioxetan 1,3-dioxetan |
1,2-dithietan 1,3-dithietan |
1,2-diselenetan 1,3-diselenetan |
3 | - | triphosphetan | - | trioxetan | trithietan | triselenetan |
4 | - | tetrafosfetan | - | tetraoxetan | tetrathietan | - |
cyclobuten
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azetin | dihydrofosfat (phosphetin) | dihydroarset | oxet | thiète | selenetus |
2 | 1,2-diazetin 1,3-diazetin |
dihydrodiphosphete | - | 1,2-dioxet 1,3-dioxet |
1,2-dithiet 1,3-dithiet |
1,2-diselenet |
3 | triazetin | dihydrotriphosphet | - | - | - | - |
4 | - | dihydrotetrafosphet | - | - | - | - |
cyclobutadien
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azete | phosphet | arsète | oxetium | thietium | - |
2 | 1,2-diazete 1,3-diazete |
1,2-diphosphet 1,3-diphosphet |
1,2-diarsæt 1,3-diarset |
- | - | - |
3 | triazet | triphosphet | - | - | - | - |
4 | tetraazet | tetrafosfet | - | - | - | - |
cyclopentan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azolidin (azolan) | phospholan | arsenolidin | tetrahydrofuran ( oxolan ) | thiolan | selenolan |
2 | 1,2-diazolidin (pyrazolidin) 1,3-diazolidin (imidazolidin) (diazolan) |
- | - | 1,2-dioxolan 1,3-dioxolan |
1,2-dithiolan 1,3-dithiolan |
1,2-diselenolan 1,3-diselenolan |
3 | 1,2,3-triazolidin 1,2,4-triazolidin (1,2,4-triazolan) |
- | - | 1,2,3-trioxolan 1,2,4-trioxolan |
1,2,3-trithiolan 1,2,4-trithiolan |
1,2,4-triselenolan |
4 | tetrazolidin (tetrazolan) | - | - | tetraoxolan | tetrathiolan | tetraselenolan |
5 | pentazolidin (cyclopentaazan eller pentazolan) | - | cyclopentaarsine | pentaoxolan | pentathiolan | pentaselenolan |
cyclopenten
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | 1- azolin (1-pyrrolin) 2-azolin (2-pyrrolin) 3-azolin (3-pyrrolin) |
dihydrophosphol | arsoline | oxol (dihydrofuran) | dihydrothiophen (thiole) |
dihydroselenophen (selenol) |
2 | 1,2-diazolin (pyrazolin) 1,3-diazolin (imidazolin) |
dihydrodiphosphol (diphospholin) |
- | 1,2-dioxol 1,3-dioxol |
dithiole | - |
3 | 1,2,3-triazolin 1,2,4-triazolin |
- | - | trioxol | trithiole | - |
4 | tetrazolin | - | - | - | - | - |
5 | pentazolin | - | - | - | - | - |
cyclopentadien
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azol ( pyrrol ) | phosphol | ydersål | furan | thiophen | selenophen |
2 | 1,2-diazol (pyrazol) 1,3-diazol ( imidazol ) |
diphosphol | diarsole | - | - | - |
3 | 1,2,3 triazol (V-triazol) 1,2,4-triazol (S-triazol) |
triphosphol | triarsole | - | - | - |
4 | tetrazol | tetrafosfol | tetraarsole | - | - | - |
5 | pentazol | pentaphosphol | - | - | - | - |
cyclohexan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | piperidin (azinan) | phosphinan | arsinane | oxan ( tetrahydropyran ) | thiane | selenan |
2 | 1,3-diazinane piperazin (1,4-diazinane) |
1,2-diphosphinan 1,3-diphoshinan 1,4-diphosphinan |
- | 1, X- dioxan , X = 2.3.4 | 1, X- dithian , X = 2,3,4 | 1, X-diselenan, X = 2.3.4 |
3 | 1,2,3-triazinan 1,2,4-triazinan 1,3,5-triazinan |
1,2,3-triphosphinan 1,2,4-triphosphinan 1,3,5-triphosphinan |
1,3,5-triarsinan | 1,2,4- trioxan 1,3,5-trioxan |
1,3,5-trithiane | 1,3,5-triselenan |
4 | 1,2,4,5-tetrazinan | 1,2,3,4-tetraphosphinan 1,2,4,5-tetraphosphinan |
- | 1,2,4,5-tetraoxan | 1,2,4,5-tetrathian | 1,2,4,5-tetraselenan |
5 | - | pentaphosphinan | - | pentaoxan | pentatisk | - |
6 | - | hexaphosphinan | - | hexaoxan | hexatisk | selen cyclohexamer (hexaselenan) |
cyclohexen
IKKE | P | Es | O | S | Se | |
---|---|---|---|---|---|---|
1 | (tetrahydropyridin) 1-piperidein 2-piperidein 3-piperidein |
1,2,3,6-tetrahydrophosphinin | - | 2,3-dihydro-2H-pyran 3,4-dihydro-2H-pyran |
dihydrothiapyran (3,4-dihydro-2H-thiopyran) δ-dihydrothiapyran (3,6-dihydro-2H-thiopyran) |
2,3-dihydroselinin |
2 | 1,2,3,6-tetrahydropyridazin 1,2,3,4-tetrahydropyridazin 1,4,5,6-tetrahydropyridazin 3,4,5,6-tetrahydropyridazin 1,2,3,4-tetrahydropyrimidin 1,2,5 , 6-tetrahydropyrimidin 1,4,5,6-tetrahydropyrimidin 1,2,3,4-tetrahydropyrazin 1,2,3,6-tetrahydropyrazin |
- | - | 3,4-dihydro-1,2-dioxin 3,6-dihydro-1,2-dioxin 2,4-dihydro-1,3-dioxin 2,3-dihydro-1,4-dioxin |
1,2- d i t hia c yclo h ex-4-en (1,2-dtch-4) 3,4-dihydrodithin = 1,2-dtch-5 4H-1,3-dithin = 1,3- dtch-4 2,3-dihydro-1,4-dithin = 1,4-dtch-2 |
dihydrodiselinin |
3 | 1,4,5,6-tetrahydrotriazin 1,2,5,6-tetrahydrotriazin 1,2,3,4-tetrahydrotriazin 3,4,5,6-tetrahydro-1,2,4-triazin 2,3,4, 5-tetrahydro-1,2,4-triazin 1,2,3,4-tetrahydro-1,2,4-triazin 1,2,5,6-tetrahydro-1,2,4-triazin 1,2,3 4-tetrahydro-1,3,5-triazin |
- | - | trioxin | 4H-1,2,3-trithiine 1,2,4-trithiine |
- |
4 | 1,2,3,4-tetrahydro-1,2,3,4-tetrazin 2,3,4,5-tetrahydro-1,2,3,4-tetrazin 3,4,5,6-tetrahydro-1, 2,3,4-tetrazin 1,4,5,6-tetrahydro-1,2,3,4-tetrazin 1,2,3,4-tetrahydro-1,2,3,5-tetrazin 2,3,4 , 5-tetrahydro-1,2,3,5-tetrazin 3,4,5,6-tetrahydro-1,2,3,5-tetrazin 1,4,5,6-tetrahydro-1,2,4,5 -tetrazin 3,4,5,6-tetrahydro-1,2,4,5-tetrazin |
- | - | tetraoxin | tetrathine (1,2,3,4-tetrathine) | - |
5 | - | - | - | - | - | - |
6 | - | - | - | - | - | - |
cyclohexadien
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | dihydroazin | 1,2-dihydrophosphinin 1,4-dihydrophosphinin |
- | 2H- pyran 4H-pyran |
2H-thiine (thiapyran) 4H-thiine |
2H-selenin (selenapyran) 4H-selenin |
2 | dihydrodiazin | dihydrodiphosphinin | 1,4-dihydro-1,4-diarsinin |
1,2-dioxin 1,4-dioxin |
1,2-dithiine 1,4-dithiine |
1,2-diselinin 1,4-diselinin |
3 | dihydrotriazin | - | - | - | - | - |
4 | dihydrotetrazin | - | - | - | - | - |
5 | dihydropentazin | - | - | - | - | - |
6 | dihydrohexazin | - | - | - | - | - |
benzen
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azin ( pyridin ) | phosphinin ( phosphorin ) | arsinin | pyranium | thiinium | seleninium (benzaselenium kation) |
2 | 1,2- diazin ( pyridazin ) 1,3-diazin ( pyrimidin ) 1,4-diazin ( pyrazin ) |
1, X-diphosphinin, X = 2,3,4 | - | - | 1,3-dithiinium 1,4-dithiinium |
- |
3 | 1,2,3- triazin 1,2,4-triazin 1,3,5-triazin |
1,3,5-triphosphinin | - | - | - | - |
4 | 1,2,3,4- tetrazin 1,2,3,5-tetrazin 1,2,4,5-tetrazin |
1,2,4,5-tetraphosphinin | - | - | - | - |
5 | pentazin | - | - | - | - | - |
6 | hexazin | hexaphosphinin | - | - | - | - |
cycloheptan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azepan | phosphepan | arsepane | oxepane | thiepane | selenepane |
2 | diazepane | diphosphepan | - | dioxepan | dithiepane | diselenepane |
3 | triazepane | - | - | trioxepan | trithiepane | triselenepane |
4 | tetraazepan | - | - | tetraoxepan | tetrathiepane | tetraselenepan |
5 | - | - | - | - | pentathiepane | - |
6 | - | - | - | - | hexathiepane | - |
7 | - | - | - | - | heptathiepane (heptasulfur) | heptaselenepan (cycloheptaselenium) |
cycloheptatrien
heteroatom | IKKE | P | Es | O | S | Se | B |
---|---|---|---|---|---|---|---|
1 | azepin | phosphepin | arsepine | oxepin | thiepin | selenepin | borepine |
2 | diazepin | diphosphepin | - | dioxepinium dioxepin svarer til en cyklus (7,2) |
dithiepinium dithiepin svarer til en cyklus (7,2) |
samme nomenklatur som O eller S | - |
3 | triazepin | triphosphepin | - | 1,2,3-trioxepin = cyklus (7,2) 1,3,5-trioxepin = cyklus (7,1) |
Samme | - | - |
4 | tetraazepin | - | - | - | 1,2,3,4- tetrathiepin = cyklus (7,1) | - | - |
5 | - | - | - | - | 1,2,3,4,5- pentathiepin = cyklus (7,1) | - | - |
6 | hexaazepin | - | - | - | - | - | - |
7 | - | - | - | - | - | - | - |
cyclooctan
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azocane | phosphocane | arsocane | oxocane | thiocane | selenocane |
2 | diazocan | diphosphocan | - | 1,3-dioxocan | 1,2-dithiocan 1,3-dithiocane 1,5-dithiocan |
1,2-selenocane 1,5-selenocane |
3 | triazocane | triphosphocan | ? | ? | ? | ? |
4 | 1,3,5,7-tetraazocan 1,2,5,6-tetraazocan |
? | ? | ? | ? | 1,3,5,7-tetraselenocan |
5 | - | ? | ? | ? | ? | ? |
6 | - | ? | ? | ? | ? | ? |
7 | - | ? | ? | ? | heptathiocan | ? |
8 | - | ? | ? | ? | ring S 8 | ? |
cyclooctatrien
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | dihydroazocin | ? | ? | oxocin | thiocin | ? |
2 | ? | ? | ? | ? | ? | ? |
3 | ? | ? | ? | ? | ? | ? |
4 | ? | ? | ? | ? | ? | ? |
5 | ? | ? | ? | ? | ? | ? |
6 | ? | ? | ? | ? | ? | ? |
7 | ? | ? | ? | ? | ? | ? |
cyclooctatetraene
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azocin | ? | ? | ? | ? | ? |
2 | ? | ? | ? | ? | ? | ? |
3 | ? | ? | ? | ? | ? | ? |
4 | ? | ? | ? | ? | ? | ? |
5 | ? | ? | ? | ? | ? | ? |
6 | ? | ? | ? | ? | ? | ? |
7 | ? | ? | ? | ? | ? | ? |
cyclononatetraene
heteroatom | IKKE | P | Es | O | S | Se |
---|---|---|---|---|---|---|
1 | azonin | ? | ? | ? | ? | ? |
2 | ? | ? | ? | ? | ? | ? |
3 | ? | ? | ? | ? | ? | ? |
4 | ? | ? | ? | ? | ? | ? |
5 | ? | ? | ? | ? | ? | ? |
6 | ? | ? | ? | ? | ? | ? |
7 | ? | ? | ? | ? | ? | ? |